Potassium Carbonate → N-Benzyl-4-methyl-2-(2-oxo-4-(2-oxoimidazolidin-1-yl)pyridin-1(2H)-yl)thiazole-5-carboxamide

HRID 1887373Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([C:8]2[S:9][C:10]([C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[C:11]([CH3:13])[N:12]=2)[C:4](=[O:24])[CH:3]=1.Cl[CH2:26][CH2:27][N:28]=[C:29]=[O:30].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:17]([NH:16][C:14]([C:10]1[S:9][C:8]([N:5]2[CH:6]=[CH:7][C:2]([N:1]3[CH2:26][CH2:27][NH:28][C:29]3=[O:30])=[CH:3][C:4]2=[O:24])=[N:12][C:11]=1[CH3:13])=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 2-(4-amino-2-oxopyridin-1(2H)-yl)-N-benzyl-4-methylthiazole-5-carboxamide (0.14 g, 0.41 mmol) in N,N-dimethylformamide (10 mL) was added 2-chloroethyl isocyanate (0.05 mL, 0.58 mmol) at ambient temperature. The resulting reaction mixture was heated at 80-90° C. for 7 hours. Potassium carbonate (0.10 g, 0.72 mmol) was added and the reaction mixture was heated for 18 hours. The solvent was removed in vacuo, and the residue was purified by column chromatography to afford the title compound in 6% yield (0.01 g): mp>300° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.76 (t, J=6.0 Hz, 1H), 8.56 (d, J=8.4 Hz, 1H), 7.64-7.17 (m, 7H), 6.08 (d, J=2.1 Hz, 1H), 4.38 (d, J=6.0 Hz, 2H), 3.85-3.79 (m, 2H), 3.42-3.37 (m, 2H), 2.60 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 161.9, 160.7, 157.8, 153.8, 150.7, 150.4, 139.9, 130.9, 128.7, 127.7, 127.2, 123.7, 101.4, 98.8, 44.3, 43.1, 36.5, 17.5; MS (ES+) m/z 410.2 (M+1).

Workup

customThe resulting reaction mixture
temperaturethe reaction mixture was heated for 18 hours
customThe solvent was removed in vacuo
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-f3107b58f82644158e381fc4ab4c17a2
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

Loading…