4-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid → 5-[2-(6-fluoro-pyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1802302Notes

Reaction equation

HRID 1802302 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]2[N:17]=[C:11]3[CH:12]=[C:13]([NH2:16])[CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[CH2:18]([O:20][C:21]([C:23]1[CH:24]=[N:25][N:26]([CH3:31])[C:27]=1[C:28](O)=[O:29])=[O:22])[CH3:19]>>[CH2:18]([O:20][C:21]([C:23]1[CH:24]=[N:25][N:26]([CH3:31])[C:27]=1[C:28](=[O:29])[NH:16][C:13]1[CH:14]=[CH:15][N:10]2[N:9]=[C:8]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=3)[N:17]=[C:11]2[CH:12]=1)=[O:22])[CH3:19]

Participants

3

Reactant 2

HCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 677744072-(6-Fluoropyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine

Product 1

HCID 677757845-[2-(6-fluoro-pyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl esterYield 40.5%

Procedure

The product was prepared in the same manner as described in example 44d using 2-(6-fluoropyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine (350 mg, 1.53 mmol) and 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (363 mg, 1.83 mmol) as starting materials. The reaction affords 5-[2-(6-fluoro-pyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (253.1 mg, 40.5%) as white solid. mp.: 290° C., MS: m/z=410.0 (M+H+).

Workup

  1. customThe product was prepared in the same manner

Sources & evidence

ORD record
ord-33d54fedac264d2ea6a6585e7096aa4b
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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