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

HRID 1887373

反応式

HRID 1887373 の反応式
[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

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 160352-Chloroethyl isocyanateHCID 249852702-(4-Amino-2-oxopyridin-1(2H)-yl)-N-benzyl-4-methylthiazole-5-carboxamide

生成物 1

HCID 57744472N-Benzyl-4-methyl-2-(2-oxo-4-(2-oxoimidazolidin-1-yl)pyridin-1(2H)-yl)thiazole-5-carboxamide収率 6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-f3107b58f82644158e381fc4ab4c17a2
出典データセット
uspto-grants-2013_08
特許番号
US08501746B2

関連ノート

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