7-Bromo-N-(5-(2-tert-butoxyethylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide → 7-Bromo-N-(4-fluoro-2-methyl-5-(2-(4-methylpiperazin-1-yl)benzylcarbamoyl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 335320Notes

Reaction equation

HRID 335320 reaction equation
[NH2:1][C:2]1[C:3]([CH3:26])=[CH:4][C:5]([F:25])=[C:6]([CH:24]=1)[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1)=[O:8].[Br:27][C:28]1[CH:33]=[CH:32][N:31]2[C:34]([C:37](NC3C=C(C(=O)NCCOC(C)(C)C)C=CC=3F)=[O:38])=[CH:35][N:36]=[C:30]2[CH:29]=1>>[Br:27][C:28]1[CH:33]=[CH:32][N:31]2[C:34]([C:37]([NH:1][C:2]3[CH:24]=[C:6]([C:7](=[O:8])[NH:9][CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[N:17]4[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]4)[C:5]([F:25])=[CH:4][C:3]=3[CH3:26])=[O:38])=[CH:35][N:36]=[C:30]2[CH:29]=1

Participants

3

Reactant 2

HCID 712834867-Bromo-N-(5-(2-tert-butoxyethylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamideHCID 866956835-Amino-2-fluoro-4-methyl-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide

Product 1

HCID 712831047-Bromo-N-(4-fluoro-2-methyl-5-(2-(4-methylpiperazin-1-yl)benzylcarbamoyl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide

Procedure

The title compound was prepared from 5-amino-2-fluoro-4-methyl-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide (step 3) analogously to 7-bromo-N-(5-(2-tert-butoxyethylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide (Intermediate 2a step 2);

Sources & evidence

ORD record
ord-c978185c3bbd40c3a9f631ea5194d078
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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