Diisopropylethylamine → 2-bromo-N-(5-(4-p-tolylthiazol-2-ylcarbamoyl)thiazol-2-yl)thiazole-5-carboxamide

HRID 1188138Notes

Reaction equation

HRID 1188138 reaction equation
[I-].ClC1C=CC=C[N+]=1C.CCN(C(C)C)C(C)C.[NH2:19][C:20]1[S:21][C:22]([C:25]([NH:27][C:28]2[S:29][CH:30]=[C:31]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)[N:32]=2)=[O:26])=[CH:23][N:24]=1.[Br:40][C:41]1[S:42][C:43]([C:46](O)=[O:47])=[CH:44][N:45]=1>CN(C=O)C>[Br:40][C:41]1[S:42][C:43]([C:46]([NH:19][C:20]2[S:21][C:22]([C:25](=[O:26])[NH:27][C:28]3[S:29][CH:30]=[C:31]([C:33]4[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=4)[N:32]=3)=[CH:23][N:24]=2)=[O:47])=[CH:44][N:45]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 27632102-Bromothiazole-5-carboxylic acidHCID 594087592-amino-N-(4-p-tolylthiazol-2-yl)thiazole-5-carboxamide

Product 1

HCID 594087532-bromo-N-(5-(4-p-tolylthiazol-2-ylcarbamoyl)thiazol-2-yl)thiazole-5-carboxamideYield 31.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-1-methylpyridinium iodide (0.048 g, 0.18 mmol), DIEA (0.045 mL, 0.25 mmol) and 2-amino-N-(4-p-tolylthiazol-2-yl)thiazole-5-carboxamide (0.04 g, 0.126 mmol) were added to a solution of 2-bromothiazole-5-carboxylic acid (26 mg, 0.126 mmol) in DMF (1 mL). The resulting solution was stirred at RT until completion of the reaction. Then a solid was precipitated with AcOEt and the solid was separated by centrifugation, yielding 2-bromo-N-(5-(4-p-tolylthiazol-2-ylcarbamoyl)thiazol-2-yl)thiazole-5-carboxamide (20 mg, 30%) as a solid that was used in the following step without further purification.

Workup

  1. customThen a solid was precipitated with AcOEt
  2. customthe solid was separated by centrifugation

Sources & evidence

ORD record
ord-98daef767ac74eba93d1fce4f0bf4489
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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