4-Acetylbenzenesulphonamide → 4-{3E-[5-(4-Isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-phenyl]-acryloyl}-benzenesulfonamide

HRID 10736노트

반응식

HRID 10736 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:14]([N:18]1[CH:22]=[N:21][N:20]=[C:19]1[C:23]1[C:24]([O:33][CH3:34])=[CH:25][C:26]([O:31][CH3:32])=[C:27]([CH:30]=1)[CH:28]=O)[CH:15]([CH3:17])[CH3:16].C[O-].[Li+]>CN(C)C=O>[CH2:14]([N:18]1[CH:22]=[N:21][N:20]=[C:19]1[C:23]1[C:24]([O:33][CH3:34])=[CH:25][C:26]([O:31][CH3:32])=[C:27](/[CH:28]=[CH:2]/[C:1]([C:4]2[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=2)=[O:3])[CH:30]=1)[CH:15]([CH3:17])[CH3:16]

참가 물질

5

반응물 3

HCID 740654-AcetylbenzenesulphonamideHCID 4177230Lithium methanolateHCID 219810255-(4-isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-benzaldehyde

생성물 1

HCID 117544734-{3E-[5-(4-Isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-phenyl]-acryloyl}-benzenesulfonamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-acetyl-benzenesulfonamide (Ex-26A, 0.12 g, 0.62 mmol) and 5-(4-isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-benzaldehyde (Ex-109E, 0.18 g, 0.62 mmol) in N,N-dimethylformamide (9 mL) was added lithium methoxide (1.0M in methanol, 2.4 mL, 2.4 mmol). The solution was allowed to stir overnight. The reaction was quenched with water. The aqueous solution was washed ethyl acetate, acidified to pH 5, extracted with dichloromethane, isopropyl alcohol (33%, v/v, in dichloromethane). The combined dichloromethane and isopropyl alcohol was washed with brine, dried over sodium sulfate and concentrated. The crude product was then stirred in ethanol (50%, v/v, in acetone) to give the title compound as a light yellow solid: m.p.>240° C. 1H NMR (DMSO-d6) δ 8.60 (s, 1H), 8.26 (d, J=8.1 Hz, 2H), 8.06 (d, J=15.3 Hz, 1H), 8.07 (s, 1H), 7.91 (d, J=8.1 Hz, 2H), 7.84 (d, J=15.3 Hz, 1H), 7.50 (s, 1H), 6.84 (s, 1H), 4.01 (s, 3H), 3.87 (s, 3H), 3.61 (d, J=7.3 Hz, 2H), 1.81–1.74 (m, 1H), 0.67 (d, J=16.7 Hz, 6H). MS m/z=471 ([M+H]+, 100%).

후처리

  1. customThe reaction was quenched with water
  2. washThe aqueous solution was washed ethyl acetate
  3. extractionextracted with dichloromethane, isopropyl alcohol (33%, v/v, in dichloromethane)
  4. washThe combined dichloromethane and isopropyl alcohol was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. stirringThe crude product was then stirred in ethanol (50%, v/v, in acetone)

출처 및 근거

ORD 기록
ord-96724e89cdcb4f12bbae30db440eb7ce
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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