HCID 12918242, compound → HCID 66856817, compound

HRID 2282276Notes

Reaction equation

HRID 2282276 reaction equation
Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3](=O)[C:4]([OH:6])=[O:5].[CH3:14][C:15]1[C:22]([C:23](=[S:25])[NH2:24])=[C:18]2[S:19][CH:20]=[CH:21][N:17]2[N:16]=1>CCO>[CH3:14][C:15]1[C:22]([C:23]2[S:25][C:2]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:3]([C:4]([OH:6])=[O:5])[N:24]=2)=[C:18]2[S:19][CH:20]=[CH:21][N:17]2[N:16]=1

Participants

4

Reactant 2

HCID 12918242HCID 12918242, compoundHCID 86649622HCID 86649622, compound

Product 1

HCID 66856817HCID 66856817, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-bromo-2-oxo-3-phenylpropanoic acid (197 mg, 1.00 mmol) and 6-methylpyrazolo[5,1-b][1,3]thiazole-7-carbothioamide (267 mg, 1.10 mmol) in EtOH (10 ml) was stirred at 50° C. for 1 h. The reaction mixture was allowed to cool to rt, the resulting precipitate was collected by filtration and then washed with EtOAc to obtain title compound (328 mg, 96%) as a colorless solid. 1H-NMR (DMSO-d6) δ 2.61 (3H, s), 7.43-7.59 (6H, m) 8.31 (1H, d, J=4.2 Hz), 12.99 (1H, br s).

Workup

  1. temperatureto cool to rt
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with EtOAc

Sources & evidence

ORD record
ord-2c5469d103b845eea046bf7274aeb88a
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

Loading…