Potassium Carbonate → N-benzyl-4-methyl-2-(2-oxopyrrolidin-1-yl)thiazole-5-carboxamide

HRID 883140Notes

Reaction equation

HRID 883140 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:17](=[O:22])[CH2:18][CH2:19][CH2:20]Br)=[N:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH2:20][CH2:19][CH2:18][C:17]2=[O:22])=[N:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86638730N-benzyl-2-(4-bromobutanamido)-4-methylthiazole-5-carboxamide

Product 1

HCID 16954473N-benzyl-4-methyl-2-(2-oxopyrrolidin-1-yl)thiazole-5-carboxamideYield 78%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of N-benzyl-2-(4-bromobutanamido)-4-methylthiazole-5-carboxamide (1.80 g, 4.54 mmol) in acetone (50 mL) and water (5 mL) was added potassium carbonate (1.50 g, 10.8 mmol) at ambient temperature. The resulting reaction mixture was stirred at ambient temperature for 2 hours. The solvent was removed in vacuo, and the residue was washed with water and t-butyl methyl ether to yield the title compound in 78% yield (1.12 g): mp 222-224° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.60 (t, J=6.0 Hz, 1H), 7.33-7.16 (m, 5H), 4.35 (d, J=6.0 Hz, 2H), 3.97 (t, J=7.2 Hz, 2H), 2.59 (t, J=7.8 Hz, 2H), 2.46 (s, 3H), 2.14-1.94 (m, 2H); MS (ES+) m/z 316.4 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent was removed in vacuo
  3. washthe residue was washed with water and t-butyl methyl ether

Sources & evidence

ORD record
ord-32be0eb1f9b34cc08bbc236a82620252
Source dataset
uspto-grants-2012_08
Patent number
US08236835B2

Reaction notes

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