5-Chloro-2-thiophenecarboxylic acid → 5-chloro-N-(4-(2-(4-(1-methylpiperidin-4-yl)piperazin-1-yl)-2-oxoethyl)thiazol-2-yl)thiophene-2-carboxamide

HRID 2237551Notes

Reaction equation

HRID 2237551 reaction equation
Br.Br.Br.[NH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[CH2:15][CH2:14]2)=[O:12])[N:9]=1.[Cl:26][C:27]1[S:31][C:30]([C:32](O)=[O:33])=[CH:29][CH:28]=1>>[CH3:25][N:22]1[CH2:23][CH2:24][CH:19]([N:16]2[CH2:15][CH2:14][N:13]([C:11](=[O:12])[CH2:10][C:8]3[N:9]=[C:5]([NH:4][C:32]([C:30]4[S:31][C:27]([Cl:26])=[CH:28][CH:29]=4)=[O:33])[S:6][CH:7]=3)[CH2:18][CH2:17]2)[CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 950485-Chloro-2-thiophenecarboxylic acidHCID 866060022-(2-Amino-thiazol-4-yl)-1-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-ethanone trihydrobromide

Product 1

HCID 426431215-chloro-N-(4-(2-(4-(1-methylpiperidin-4-yl)piperazin-1-yl)-2-oxoethyl)thiazol-2-yl)thiophene-2-carboxamide

Procedure

In analogy to example 47.3, 2-(2-amino-thiazol-4-yl)-1-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-ethanone trihydrobromide (example 47.2) was coupled with 5-chlorthiophene-2-carboxylic acid, using general method D, to give 5-chloro-thiophene-2-carboxylic acid (4-{2-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-thiazol-2-yl)-amide. Light orange solid. MS 468.5 ([M+H]+)

Sources & evidence

ORD record
ord-67e3f2aadb1a4503acb151555a4b46fe
Source dataset
uspto-grants-2010_05
Patent number
US07718659B2

Reaction notes

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