4-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid → 5-[2-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1802278Notes

Reaction equation

HRID 1802278 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:18]=[C:12]2[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][N:11]2[N:10]=1.[CH2:19]([O:21][C:22]([C:24]1[CH:25]=[N:26][N:27]([CH3:32])[C:28]=1[C:29](O)=[O:30])=[O:23])[CH3:20]>>[CH2:19]([O:21][C:22]([C:24]1[CH:25]=[N:26][N:27]([CH3:32])[C:28]=1[C:29](=[O:30])[NH:17][C:14]1[CH:15]=[CH:16][N:11]2[N:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[N:18]=[C:12]2[CH:13]=1)=[O:23])[CH3:20]

Participants

3

Reactant 2

HCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 677742602-(2-Methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine

Product 1

HCID 677756495-[2-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl esterYield 64.2%

Procedure

The product was prepared in the same manner as described in example 28 using 2-(2-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine (365 mg, 1.52 mmol) and 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (331 mg, 1.67 mmol) as starting material. The reaction affords 5-[2-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (410 mg, 64.2%) as white solid. MS: m/z=421.1 (M+H+).

Workup

  1. customThe product was prepared in the same manner

Sources & evidence

ORD record
ord-f0578152b87e4eb689e75733cdfe41ab
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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