Lithium methanolate → 4-{3E-[4-Methoxy-2-(2-morpholin-4-yl-ethoxy)-5-thiophen-2-yl-phenyl]-acryloyl}-benzamide

HRID 10715

반응식

HRID 10715 반응식
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[N:13]1([CH2:19][CH2:20][O:21][C:22]2[CH:29]=[C:28]([O:30][CH3:31])[C:27]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)=[CH:26][C:23]=2[CH:24]=O)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C[O-].[Li+]>CN(C=O)C.CO>[CH3:31][O:30][C:28]1[C:27]([C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)=[CH:26][C:23](/[CH:24]=[CH:2]/[C:1]([C:4]2[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[O:9])=[CH:6][CH:5]=2)=[O:3])=[C:22]([O:21][CH2:20][CH2:19][N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[CH:29]=1

참가 물질

6

반응물 3

HCID 4177230Lithium methanolateHCID 111594974-AcetylbenzamideHCID 161161844-Methoxy-2-(2-morpholin-4-ylethoxy)-5-thien-2-ylbenzaldehyde

생성물 1

HCID 103909574-{3E-[4-Methoxy-2-(2-morpholin-4-yl-ethoxy)-5-thiophen-2-yl-phenyl]-acryloyl}-benzamide수율 57.1%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-acetyl-benzamide (Ex-92A, 0.25 g, 1.53 mmol) and 2-(2-morpholin-4-yl-ethoxy)-4-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-60A, 0.53 g, 1.53 mmol) in DMF (7 mL) and methanol (3 mL) was added lithium methoxide. The solution was allowed to stir at ambient temperature. The reaction was quenched with water after 2 hours. The aqueous solution was extracted with ethyl acetate. The combined extract was washed with NaHCO3, NH4Cl, brine, dried (Na2SO4) and concentrated. The residue was stirred in ethanol overnight to afford the title compound as a yellow solid (0.43 g, 57%), mp 183–184° C. 1H-NMR (CDCl3) δ 8.09–8.04 (m, 3H), 7.93 (d, J=8.3 Hz, 2H), 7.87 (s, 1H), 7.57 (d, J=15.7 Hz, 1H), 7.42 (d, J=3.9 Hz, 1H), 7.32 (d, 4.4 Hz, 1H), 7.11–7.08 (m, 1H), 6.55 (s, 1H), 6.25 (bs, 1H), 5.75 (bs, 1H), 4.25 (t, J=5.9 Hz, 2H), 3.98 (s, 3H), 3.71 (t, J=4.2 Hz, 4H), 2.92 (t, J=5.7 Hz, 2H), 2.59 (t, J=4.6 Hz, 4H). MS m/z=493 ([M+H]+, 100%).

후처리

  1. customThe reaction was quenched with water after 2 hours
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. extractionThe combined extract
  4. washwas washed with NaHCO3, NH4Cl, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. stirringThe residue was stirred in ethanol overnight

출처 및 근거

ORD 기록
ord-65a52f3bb4944230af47e3a45db65550
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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