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

HRID 1188139Notes

Reaction equation

HRID 1188139 reaction equation
Br[C:2]1[S:3][C:4]([C:7]([NH:9][C:10]2[S:11][C:12]([C:15](=[O:29])[NH:16][C:17]3[S:18][CH:19]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)[N:21]=3)=[CH:13][N:14]=2)=[O:8])=[CH:5][N:6]=1>C(N)CC>[CH2:5]([NH:6][C:2]1[S:3][C:4]([C:7]([NH:9][C:10]2[S:11][C:12]([C:15](=[O:29])[NH:16][C:17]3[S:18][CH:19]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)[N:21]=3)=[CH:13][N:14]=2)=[O:8])=[CH:5][N:6]=1)[CH2:4][CH3:7]

Participants

3

Reactant 1

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

Product 1

HCID 866434762-(propylamino)-N-(5-(4-p-tolylthiazol-2-ylcarbamoyl)thiazol-2-yl)thiazole-5-carboxamideYield 206.3%

Reagents, catalysts & solvents 1

HCID 7852PropylamineSolvent

Procedure

A solution of 2-bromo-N-(5-(4-p-tolylthiazol-2-ylcarbamoyl)thiazol-2-yl)thiazole-5-carboxamide (15 mg, 0.03 mmol) in neat propylamine (0.5 mL) was stirred at reflux for 24 hrs. The solvent was evaporated and the crude product was purified by column chromatography (0%-5% MeOH/AcOEt) yielding 2-(propylamino)-N-(5-(4-p-tolylthiazol-2-ylcarbamoyl)-thiazol-2-yl)thiazole-5-carboxamide (15 mg, 17%).

Workup

  1. temperatureat reflux for 24 hrs
  2. customThe solvent was evaporated
  3. customthe crude product was purified by column chromatography (0%-5% MeOH/AcOEt)

Sources & evidence

ORD record
ord-40580cdb7cbf43dd8e6cb93415af0dfa
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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