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

HRID 1887306

반응식

HRID 1887306 반응식
[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

참가 물질

6

반응물 4

HCID 240Benzaldehyde2회HCID 6422Trifluoroacetic acidHCID 12052Triethylsilane2회HCID 249852702-(4-Amino-2-oxopyridin-1(2H)-yl)-N-benzyl-4-methylthiazole-5-carboxamide

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5ac9deebdf284ecda21217d70b30c7b4
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501746B2

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