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

Base Information

• Chemical Name: 4-[[5-[(Methoxyamino)carbonyl]-2-methylphenyl]amino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid
• CAS No.: 1005196-62-2
• Molecular Formula: C₁₇H₁₇N₅O₄
• Molecular Weight: 355.353
• DSSTox Substance ID: DTXSID501109446
• Mol file: 1005196-62-2.mol

Synonyms:DTXSID501109446;1005196-62-2;4-[[5-[(Methoxyamino)carbonyl]-2-methylphenyl]amino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid

Chemical Property of 4-[[5-[(Methoxyamino)carbonyl]-2-methylphenyl]amino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 355.12805404
• Heavy Atom Count: 26
• Complexity: 533

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C=C(C=C1)C(=O)NOC)NC2=NC=NN3C2=C(C(=C3)C(=O)O)C

Technology Process of 4-[[5-[(Methoxyamino)carbonyl]-2-methylphenyl]amino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid

There total 15 articles about 4-[[5-[(Methoxyamino)carbonyl]-2-methylphenyl]amino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid 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-((5-(methoxycarbamoyl)-2-methylphenyl)-amino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (427877-66-5) → 4-((5-(methoxycarbamoyl)-2-methylphenyl)amino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid (1005196-62-2)

Guidance literature:

With sodium hydroxide; In water; at 60 - 65 ℃; for 6h;

DOI:10.1021/op300181r

Reference yield: 69.0%

methyl 4-(2-methyl-5-(methoxycarbamoyl)phenylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (1005196-65-5) → 4-((5-(methoxycarbamoyl)-2-methylphenyl)amino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid (1005196-62-2)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; methanol; at 60 ℃;

DOI:10.1016/j.bmcl.2014.07.017

Reference yield:

ethyl 2-(((2-ethoxy-2-oxoethyl)amino)methylene)-3-oxobutanoate → 4-((5-(methoxycarbamoyl)-2-methylphenyl)amino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid (1005196-62-2)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium 2-methylbutan-2-olate; ethyl trifluoroacetate, / ethanol; toluene / 9 h / 60 - 63 °C / Large scale

2: potassium tert-butylate / 1-methyl-pyrrolidin-2-one; tetrahydrofuran / 20 - 37 °C / Large scale

3: formamide; phosphoric acid / 120 °C

4: trichlorophosphate; N-ethyl-N,N-diisopropylamine / toluene / 2 h / 110 °C

5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 58 °C / Large scale

6: sodium hydroxide / water / 6 h / 60 - 65 °C

With ethyl trifluoroacetate,; phosphoric acid; potassium tert-butylate; potassium 2-methylbutan-2-olate; formamide; N-ethyl-N,N-diisopropylamine; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/op300181r

upstream raw materials:

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

ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate

3-methyl-1H-pyrrole-2,4-dicarboxylic acid diethyl ester

1-amino-3-methyl-1H-pyrrole-2,4-dicarboxylic acid diethyl ester

Downstream raw materials:

4-[[5-[(Methoxyamino)carbonyl]-2-methylphenyl]amino]-5-methyl-N-[2-(4-morpholinyl)ethyl]pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide

4-[[5-[(Methoxyamino)carbonyl]-2-methylphenyl]amino]-5-methyl-N-(2-pyridinylmethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide

N-n-propyl-4-(2-methyl-5-(methoxycarbamoyl)phenylamino)-5-methylpyrrolo-[2,1-f][1,2,4]triazine-6-carboxamide

C₁₈H₂₀N₆O₃