Benzaldehyde → N-benzyl-2-(4-(benzylamino)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

HRID 1887306

反応式

HRID 1887306 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.FC(F)(F)C(O)=O.[CH:32](=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C([SiH](CC)CC)C>C(Cl)(Cl)Cl>[CH2:17]([NH:16][C:14]([C:10]1[S:9][C:8]([N:5]2[CH:6]=[CH:7][C:2]([NH:1][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[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

6

反応物 4

HCID 240Benzaldehyde2 回HCID 6422Trifluoroacetic acidHCID 12052Triethylsilane2 回HCID 249852702-(4-Amino-2-oxopyridin-1(2H)-yl)-N-benzyl-4-methylthiazole-5-carboxamide

生成物 1

HCID 57744502N-benzyl-2-(4-(benzylamino)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide収率 79.2%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a solution of 2-(4-amino-2-oxopyridin-1(2H)-yl)-N-benzyl-4-methylthiazole-5-carboxamide (0.30 g, 0.88 mmol) and trifluoroacetic acid (15 mL) in chloroform (20 mL) was added benzaldehyde (0.10 mL, 0.98 mmol). The reaction mixture was stirred for 15 minutes at ambient temperature, then triethylsilane (0.15 mL, 1.00 mmol) was added. The reaction mixture was kept stirring for 2 hours at ambient temperature, then another portion of benzaldehyde (0.10 mL, 0.98 mmol) and triethylsilane (0.15 mL, 1.00 mmol) was added. The reaction mixture was kept stirring for another 2 hours at ambient temperature. The solvent was removed in vacuo, and the residue was washed with saturated aqueous sodium bicarbonate solution, water and t-butylmethyl ether to afford the title compound (0.30 g, 79%): mp 253-255° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.68 (t, J=5.7 Hz, 1H), 8.39 (d, J=7.8 Hz, 1H), 7.87 (s, 1H), 7.44-7.21 (m, 10H), 6.21 (d, J=7.8 Hz, 1H), 5.31 (s, 1H), 4.36 (d, J=5.7 Hz, 2H), 4.31 (d, J=4.5 Hz, 2H), 2.50 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.1, 160.9, 155.9, 154.5, 150.2, 140.0, 138.3, 130.6, 128.9, 128.7, 127.7, 127.6, 127.1, 122.8, 103.6, 88.6, 46.0, 43.0, 17.5; MS (ES+) m/z 431.2 (M+1).

後処理

  1. stirringThe reaction mixture was kept stirring for 2 hours at ambient temperature
  2. stirringThe reaction mixture was kept stirring for another 2 hours at ambient temperature
  3. customThe solvent was removed in vacuo
  4. washthe residue was washed with saturated aqueous sodium bicarbonate solution, water and t-butylmethyl ether

出典と根拠

ORDレコード
ord-5ac9deebdf284ecda21217d70b30c7b4
出典データセット
uspto-grants-2013_08
特許番号
US08501746B2

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