Pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid, 4-[[1-[(3-fluorophenyl)methyl]-1H-indazol-5-yl]amino]-5-methyl-

Base Information

• Chemical Name: Pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid, 4-[[1-[(3-fluorophenyl)methyl]-1H-indazol-5-yl]amino]-5-methyl-
• CAS No.: 856667-80-6
• Molecular Formula: C22H17 F N6 O2
• Molecular Weight: 416.414
• Mol file: 856667-80-6.mol

Synonyms:Pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid, 4-[[1-[(3-fluorophenyl)methyl]-1H-indazol-5-yl]amino]-5-methyl-

Chemical Property of Pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid, 4-[[1-[(3-fluorophenyl)methyl]-1H-indazol-5-yl]amino]-5-methyl-

Chemical Property:

• PSA: 97.34000
• LogP: 4.08960

Purity/Quality:

98%min ^*data from raw suppliers

4-(1-(3-fluorobenzyl)-1H-indazol-5-ylamino)-5-methylpyrrolo[1,2-f][1,2,4]triazine-6-carboxylicacid 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid, 4-[[1-[(3-fluorophenyl)methyl]-1H-indazol-5-yl]amino]-5-methyl-

There total 7 articles about Pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid, 4-[[1-[(3-fluorophenyl)methyl]-1H-indazol-5-yl]amino]-5-methyl- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

ethyl 4-[1-(3-fluoro-benzyl)-1H-indazol-5-ylamino]-5-methyl-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (856667-79-3) → 4-(1-(3-fluorobenzyl)-1H-indazol-5-ylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid (856667-80-6)

Guidance literature:

ethyl 4-[1-(3-fluoro-benzyl)-1H-indazol-5-ylamino]-5-methyl-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate; With sodium hydroxide; water; In tetrahydrofuran; methanol; at 5 - 60 ℃; for 4h;

With hydrogenchloride; In tetrahydrofuran; methanol; at 35 ℃; pH=3;

Reference yield:

5-nitroindazole (5401-94-5) → 4-(1-(3-fluorobenzyl)-1H-indazol-5-ylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid (856667-80-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: caesium carbonate / N,N-dimethyl-formamide / 1.25 h / 70 - 80 °C

2.1: hydrogen / tetrahydrofuran / 1 h / 30 - 40 °C / 775.74 Torr

3.1: N-ethyl-N,N-diisopropylamine / 70 - 80 °C

4.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 5 - 60 °C

4.2: 35 °C / pH 3

With sodium hydroxide; water; hydrogen; caesium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

Reference yield:

1-(3-fluorobenzyl)-1H-indazol-5-ylamine (202197-31-7) → 4-(1-(3-fluorobenzyl)-1H-indazol-5-ylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid (856667-80-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine / 70 - 80 °C

2.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 5 - 60 °C

2.2: 35 °C / pH 3

With sodium hydroxide; water; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol;

upstream raw materials:

ethyl 4-[1-(3-fluoro-benzyl)-1H-indazol-5-ylamino]-5-methyl-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

4-chloro-5-methyl-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid ethyl ester

1-(3-fluorobenzyl)-5-nitro-1H-carbazole

1-(Bromomethyl)-3-fluorobenzene

Downstream raw materials:

(S)-tert-butyl 3-((4-(1-(3-fluorobenzyl)-1H-indazol-5-ylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-ylcarbamoyloxy)methyl)morpholine-4-carboxylate

[4-[[1-(3-fluorophenyl)methyl]-1H-indazol-5-ylamino]-5-methyl-pyrrolo[2,1-f][1,2,4]triazin-6-yl]carbamic acid (3S)-3-morpholinylmethyl ester

Refernces

• 1、 Gavai, Ashvinikumar V.,Fink, Brian E.,Fairfax, David J.,Martin, Gregory S.,Rossiter, Lana M.,Holst, Christian L.,Kim, Soong-Hoon,Leavitt, Kenneth J.,Mastalerz, Harold,Han, Wen-Ching,Norris, Derek,Goyal, Bindu,Swaminathan, Shankar,Patel, Bharat,Mathur, Arvind,Vyas, Dolatrai M.,Tokarski, John S.,Chiang, Yu,Oppenheimer, Simone,Hongjian, Zhang,Marathe, Punit,Fargnoli, Joseph,Lee, Francis Y.,Wong, Tai W.,Vite, Gregory D.. "Discovery and preclinical evaluation of [4-[[1-(3-fluorophenyl)methyl]-1H- indazol-5-ylamino]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]carbamic acid, (3S)-3-morpholinylmethyl ester (BMS-599626), a selective and orally efficacious inhibitor of human epide". supporting information; experimental part. p. 6527 - 6530. Retrieved 2010/03/26.