2-Chloropyrimidin-5-amine → N-(2-Chloropyrimidin-5-yl)-5-trifluoromethyl-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HRID 1690069Notes

Reaction equation

HRID 1690069 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12](O)=[O:13])[N:9]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:6]2=[N:7][CH:8]=1.[Cl:25][C:26]1[N:31]=[CH:30][C:29]([NH2:32])=[CH:28][N:27]=1>>[Cl:25][C:26]1[N:31]=[CH:30][C:29]([NH:32][C:12]([C:10]2[N:9]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:6]3=[N:7][CH:8]=[C:3]([C:2]([F:24])([F:1])[F:23])[CH:4]=[C:5]3[CH:11]=2)=[O:13])=[CH:28][N:27]=1

Participants

3

Reactant 2

HCID 122159932-Chloropyrimidin-5-amineHCID 668635175-Trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid

Product 1

HCID 86639061N-(2-Chloropyrimidin-5-yl)-5-trifluoromethyl-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamideYield 22.9%

Procedure

According to a method similar to that described in Stage 1.4, starting from 1.08 g (3.2 mmol) of 5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid, described in Stage 1.3, and 0.46 g (3.52 mmol) of 2-chloro-5-aminopyrimidine, we obtain 0.33 g of the expected product.

Sources & evidence

ORD record
ord-d1cd566918ef494eb76b4fc843e339c0
Source dataset
uspto-grants-2012_04
Patent number
US08153650B2

Reaction notes

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