4-Chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid methyl ester

Base Information

• Chemical Name: 4-Chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid methyl ester
• CAS No.: 310442-40-1
• Molecular Formula: C9H8 Cl N3 O2
• Molecular Weight: 225.634
• Hs Code.: 2933990090
• Mol file: 310442-40-1.mol

Synonyms:4-Chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylicacid methyl ester

Chemical Property of 4-Chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid methyl ester

Chemical Property:

• PKA: -3.72±0.30(Predicted)
• PSA: 56.49000
• Density: 1.48±0.1 g/cm3(Predicted)
• LogP: 1.47770

Purity/Quality:

98%min ^*data from raw suppliers

Methyl4-chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid methyl ester

There total 8 articles about 4-Chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid methyl ester 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: 93.0%

5-methyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid methyl ester (310431-29-9) → methyl 4-chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (310442-40-1)

Guidance literature:

With trichlorophosphate; at 100 ℃; for 15h; Product distribution / selectivity;

Reference yield:

methyl 4-methyl-5-(2,2,2-trichloroacetyl)-1H-pyrrole-3-carboxylate → methyl 4-chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (310442-40-1)

Guidance literature:

Multi-step reaction with 4 steps

1: NaOMe

2: Ph₂P(O)ONH₂; NaH / dimethylformamide

3: Heating

4: POCl₃ / Heating

With O-(diphenylphosphinyl)hydroxylamine; sodium methylate; sodium hydride; trichlorophosphate; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.12.079

Reference yield:

methyl 4-methyl-1H-pyrrole-3-carboxylate (40318-15-8) → methyl 4-chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (310442-40-1)

Guidance literature:

Multi-step reaction with 5 steps

1: AlCl₃

2: NaOMe

3: Ph₂P(O)ONH₂; NaH / dimethylformamide

4: Heating

5: POCl₃ / Heating

With aluminium trichloride; O-(diphenylphosphinyl)hydroxylamine; sodium methylate; sodium hydride; trichlorophosphate; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.12.079

upstream raw materials:

5-methyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid methyl ester

dimethyl 1-amino-3-methyl-1H-pyrrole-2,4-dicarboxylate

methyl 4-methyl-1H-pyrrole-3-carboxylate

dimethyl 3-methyl-1H-pyrrole-2,4-dicarboxylate

Downstream raw materials:

4-((5-(methoxycarbamoyl)-2-methylphenyl)amino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid

methyl 4-(2-methyl-5-(ethoxycarbamoyl)phenylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

4-(2-methyl-5-(ethoxycarbamoyl)phenylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid

Refernces

• 1、 Wang, Min,Gao, Mingzhang,Zheng, Qi-Huang. "Synthesis of carbon-11-labeled 4-(phenylamino)-pyrrolo[2,1-f][1,2,4] triazine derivatives as new potential PET tracers for imaging of p38α mitogen-activated protein kinase". . p. 3700 - 3705. Retrieved 2014/09/17.
• 2、 Borzilleri, Robert M.,Cai, Zhen-Wei,Ellis, Christopher,Fargnoli, Joseph,Fura, Aberra,Gerhardt, Tracy,Goyal, Bindu,Hunt, John T.,Mortillo, Steven,Qian, Ligang,Tokarski, John,Vyas, Viral,Wautlet, Barri,Zheng, Xioping,Bhide, Rajeev S.. "Synthesis and SAR of 4-(3-hydroxyphenylamino)pyrrolo[2,1-f][1,2,4]triazine based VEGFR-2 kinase inhibitors". . p. 1429 - 1433. Retrieved 2007/10/03.