Category: 918538-05-3

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

Weigh the intermediate 1-e (50 mg, 0.27 mmol)1-methyl-1H-pyrazole-4-boronic acid pinacol ester (55 mg, 0.27 mmol)2N aqueous Na2CO3 solution (0.27 ml, 0.54 mmol)Bis (triphenylphosphine) palladium (II) chloride (19 mg, 0.027 mmol)Dioxane (5 ml) was added to the flask and heated to 70 C for 16 h.After stopping the reaction,To the reaction solution was added 100 ml of water,Stir,Ethyl acetate (20 ml * 4)Drying the ester layer with anhydrous sodium sulfate,Concentrated, separated by column chromatography (petroleum ether: ethyl acetate = 5: 1),A yellow solid (55 mg, 88%) was obtained.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 918538-05-3.

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Xin Minxing; Wen Jun; Tu Chongxing; Liu Zhaoyu; Shen Han; Wang Mengyu; Zhao Xinge; (36 pag.)CN104003990; (2017); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. COA of Formula: C6H3Cl2N3

To a 100 mL flask was added 2,4-dichloropyrrolo[2,l-^[l,2,4]triazine (3 g, 15.96 mmol), tetrahydrofuran (40 mL) and stirred. To the resulting solution was portionwise added sodium phenolate (2.038 g, 17.55 mmol). After 1 h, an aliquot of the reaction mixture was diluted with methanol and anlayzed by LCMS to ensure complete conversion. The reaction mixture was concentrated. To the residue was added water, stirred, filtered and dried. Obtained 2-chloro-4-phenoxypyrrolo[2,l- |[l,2,4]triazine (3.71 g, 15.10 mmol, 95 % yield) as an off-white solid. LCMS: RT = 1.05 min; MS(ES): m/z observed = 245.9, 247.9 (Injection conditions: Column: Waters Acquity UPLC BEH C18, 2.1 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 100% water with 0.05% TFA; Mobile Phase B: 100% MeCN with 0.05% TFA; Gradient: 2-98% B over 1 minute, then a 0.5- minute hold at 98% B; Flow: 0.8 mL/min; Detection: UV at 220 nm); NMR (300 MHz, DMSO-de) delta 8.13 (dd, J=2.6, 1.5 Hz, 1H), 7.56 – 7.48 (m, 2H), 7.42 – 7.34 (m, 3H), 7.15 (dd, J=4.5, 1.5 Hz, 1H), 6.99 (dd, J=4.5, 2.6 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 918538-05-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BORZILLERI, Robert M.; FINK, Brian E.; HARIKRISHNAN, Lalgudi S.; WARRIER, Jayakumar Sankara; (87 pag.)WO2017/40448; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 918538-05-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 918538-05-3 name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

In a 25mL reaction vial, Pd(PPh3)2Cl2 (19mg, 0.027mmol) and 2N Na2CO3 solution (0.27mL, 0.54mmol) were added to a solution of 1-methyl-1H-pyrazole-4-boronic acid pinacol ester (55mg, 0.27mmol) and 12 (50mg, 0.27mmol) in dioxane (5mL). The mixture was stirred at 70C for 16h under N2 atmosphere. The reaction mixture was cooled to room temperature and filtrated. The filtrate was diluted with H2O (100mL) and then extracted with EtOAc, and the organic layer was dried over anhydrous Na2SO4, After filtration, the filtrate was evaporated and purified by chromatography (petroleum ether/EtOAc, 5:1) to give the product 20 as a yellow solid (55mg, 88%). MS (ESI) m/z: [M+H]+=234. 1H NMR (400M, DMSO-d6) delta 8.87 (s, 1H, ArH), 8.38 (s, 1H, ArH), 8.14 (s, 1H, ArH), 7.53 (d, 1H, J=4.8Hz, ArH), 7.10 (dd, 1H, J1=2.4Hz, J2=4.8Hz, ArH), 3.98 (s, 3H, ArCH3) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, and friends who are interested can also refer to it.

Reference:
Article; Xin, Minhang; Zhang, Liandi; Tang, Feng; Tu, Chongxing; Wen, Jun; Zhao, Xinge; Liu, Zhaoyu; Cheng, Lingfei; Shen, Han; Bioorganic and Medicinal Chemistry; vol. 22; 4; (2014); p. 1429 – 1440;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

EXAMPLE 1N2-((15)-l-cyclohexylethyl)-N4-(3-cyclopropyl-/H-pyrazol-5-yl)pyrrolo[2,l-J] [l,2,4]triazine-2,4-diamineIA. Preparation of 2-chloro-N-(3-cyclopropyl-7H-pyrazol-5-yl)pyrrolo[l,2- f [l,2,4]triazin-4-amine[0078] A solution of 2,4-dichloropyrrolo[l,2-/|[l,2,4]triazine (1.5 g, 5.3 mmol) in z-PrOeta (15 mL) was treated with S-cyclopropyl-iH-pyrazol-S-amine (657 mg, 5.3 mmol) and DIEA (0.92 mL, 5.3 mmol). The reaction was stirred overnight at ambient temperature and then filtered. The filter cake was washed with cold /-PrOH and dried under vacuum to afford IA as a solid (1.3 g, 90%). HPLC tR = 3.301 min (YMC S5 Combiscreen ODS 4.6 x 50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm). [M+H]+ = 275.37 ‘. EXAMPLE 43 2-((4-((3-cyclopropyl-lH-pyrazol-5-yl)amino)pyrrolo[2,l-/| [l,2,4]triazin-2- yl)amino)-N-l,3-thiazol-2-ylacetamide43 A. Preparation of 2-chloro-N-(3-cyclopropyl-7H-pyrazol-5-yl)pyrrolo [1,2- /][l,2,4]triazin-4-amine [0085] A solution of 2,4-dichloropyrrolo[l,2-/|[l,2,4]triazine (1.5 g, 5.3 mmol) in i-PrOH (15 mL) was treated with S-cyclopropyl-iH-pyrazol-S-amine (657 mg, 5.3 mmol) and DIEA (0.92 mL, 5.3 mmol). The reaction was stirred overnight at ambient temperature and then filtered. The filter cake was washed with cold i-PrOeta and dried under vacuum to afford 43A as a solid (1.3 g, 90%). etaPLC tR = 3.301 min (YMC S5 Combiscreen ODS 4.6 x 50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm). [M+H]+ = 275.37.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 918538-05-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/21859; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H3Cl2N3

General procedure: Compound 183a was prepared from tert-butyl 2,4-dichloro-5,6-dihydropyrido[3,4- d]pyrimidine-7(8H)-carboxylate (182a) (1.0 g, 3.29 mmol) in 2-Propanol (15 mL) using DIPEA (2.3 mL, 13.15 mmol) and 1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-amine (57a) (0.98 g, 3.95 mmol). This gave after workup and purification by flash column chromatography [silica gel, (12 g) eluting with DMA-80 in DCM (0 to 80%)] fert-butyl 2-chloro-4-((l-(3,4,5- trimethoxyphenyl)-lH-imidazol-4-yl)amino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)- carboxylate (183a) (0.87 g, 51 % yield) as a buff solid; NMR (300 MHz, DMSO-^e) delta 9.65 (s, 1H, D20 exchangeable), 8.16 (d, J = 1.5 Hz, 1H), 7.78 (d, J = 1.6 Hz, 1H), 6.90 (s, 2H), 4.35 (s, 2H), 3.87 (s, 6H), 3.69 (s, 3H), 3.61 (t, J = 5.8 Hz, 2H), 2.69 – 2.60 (m, 2H), 1.43 (s, 9H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 918538-05-3.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 918538-05-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 – 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 – 3.82 (m, 1H), 3.72 – 3.39 (m, 2H), 2.22 – 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).

The chemical industry reduces the impact on the environment during synthesis 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 918538-05-3,Some common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Compound 5 (80 mg, 0.424 mmol) was weighed out,P-trifluoromethoxybenzeneboronic acid (90 mg, 0.44 mmol)Triethylamine (121 mg, 1.2 mmol)Bis (triphenylphosphine) palladium (II) chloride (30 mg, 0.042 mmol)DMF (28.5 ml), water (0.5 ml) was added to the flask and heated to 80 C for 4 h.After stopping the reaction, 100 ml of water was added to the reaction solution,Stirred, extracted with ethyl acetate (20 ml * 4)The ester layer was dried over anhydrous sodium sulfate, concentrated,Column chromatography (petroleum ether: ethyl acetate = 20: 1) gave a yellow solid (97 mg, 77.6%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, its application will become more common.

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Xin Minxing; Wen Jun; Tu Chongxing; Liu Zhaoyu; Shen Han; Wang Mengyu; Zhao Xinge; (36 pag.)CN104003990; (2017); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 918538-05-3

To a 100 mL flask was added 2,4-dichloropyrrolo[2,1-J][1,2,4]triazine (3 g, 15.96 mmol), tetrahydrofuran (40 mL) and stirred. To the resulting solution was portionwise added sodium phenolate (2.03 8 g, 17.55 mmol). After 1 h, an aliquot of the reaction mixture was diluted with methanol and anlyzed by LCMS to ensure complete conversion. The reaction mixture was concentrated. To the residue was added water, stirred, filtered, washed extensively with water and dried. Obtained 2-chloro-4-phenoxypyrrolo[2, 1-J][1,2,4]triazine (3.71 g, 15.10 mmol, 95 % yield) as an off-while solid. LCMS m/z 245.9(M+H); rt 1.05 mm; Conditions A. ?HNMR: (300 IVIHz, DMSO-d6) oe 8.13 (dd, J2.6,1.5 Hz, 1H), 7.56-7.48 (m, 2H), 7.42-7.34 (m, 3H), 7.15 (dd, J4.5, 1.5 Hz, 1H), 6.99 (dd, J4.5, 2.6 Hz, 1H).

The synthetic route of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARIKRISHNAN, Lalgudi S.; FINK, Brian E.; BORZILLERI, Robert M.; TONUKUNURU, Gopikishan; RAHAMAN, Hasibur; WARRIER, Jayakumar Sankara; SESHADRI, Balaji; (411 pag.)WO2017/15425; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Application In Synthesis of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

General procedure: In a 50mL reaction vial, Pd(PPh3)2Cl2 (30mg, 0.042mmol) and NEt3 (121mg, 1.2mmol) were added to a solution of 12 (80mg, 0.424mmol) and 4-trifluoromethoxylphenylboronic acid (90mg, 0.44mmol) in DMF (28.5mL) and H2O (0.5mL). The mixture was stirred at 80C for 4h under N2 atmosphere. The reaction mixture was cooled to room temperature and filtrated. The filtrate was diluted with H2O (100mL) and then extracted with EtOAc, and the organic layer was dried over anhydrous Na2SO4, after filtration, the filtrate was evaporated and purified by chromatography (petroleum ether/EtOAc, 20:1) to give the product 13 as a yellow solid (97mg, 78%).

The synthetic route of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xin, Minhang; Zhang, Liandi; Tang, Feng; Tu, Chongxing; Wen, Jun; Zhao, Xinge; Liu, Zhaoyu; Cheng, Lingfei; Shen, Han; Bioorganic and Medicinal Chemistry; vol. 22; 4; (2014); p. 1429 – 1440;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

To a solution of 2,4-dichloropyrrolo[2,l-f [l,2,4]triazine (la) (3 g, 15.96 mmol, CASNo. 918538-05-3) in DMF (50 mL) under Ar atmosphere was added 1 -ethoxy vi nyltri -//-butylti n (7.07 mL, 20.74 mmol, CASNo. 97674-02-7) and bis(triphenylphosphine)Palladium(II)chloride (0.56 g, 0.8 mmol). The mixture was heated with stirring at 100 C for 30 min, cooled to room temp and diluted with EtOAc (150 mL). The reaction mixture was washed with water (50 mL), brine (30 mL), dried, filtered and concentrated in vacuum to dryness. The residue obtained was purified by flash column chromatography [silica (24 g), eluting with EtOAc in hexane from 0-50%] to afford 2-chl oro-4-(l -ethoxy vinyl)pyrrolo[2, l-f][l, 2, 4]triazine (lb) (2.2 g, 62 % yield) as an orange oil; NMR (300 MHz, DMSO-7e) d 8.23 (dd, J= 2.6, 1.4 Hz, 1H), 7.34 (dd, J= 4.7, 1.4 Hz, 1H), 7.11 (dd, j= 4.7, 2.6 Hz, 1H), 5.64 (d, 7= 2.4 Hz, 1H), 4.88 (d, J= 2.4 Hz, 1H), 4.03 (q, J= 7.0 Hz, 2H), 1.44 (t, J= 7.0 Hz, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 918538-05-3.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda; ZHANG, Weihe; LU, Pen-Cheng; WU, Minwan; LV, Wei; NGUYEN, Trung, Xuan; DANG, Zhao; CHINTAREDDY, Venkat, R.; KUMAR, V., Satish; RAMAN, Krishnan; (1223 pag.)WO2019/195720; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics