4-Acetylbenzenesulphonamide → HCID 178419032, 화합물

HRID 10738노트

반응식

HRID 10738 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].[CH:14]1([C:17]2[NH:18][CH:19]=[C:20]([C:22]3[C:23]([O:32][CH3:33])=[CH:24][C:25]([O:30][CH3:31])=[C:26]([CH:29]=3)[CH:27]=O)[N:21]=2)[CH2:16][CH2:15]1.C[O-].[Li+]>CN(C)C=O>[CH:14]1([C:17]2[NH:18][CH:19]=[C:20]([C:22]3[C:23]([O:32][CH3:33])=[CH:24][C:25]([O:30][CH3:31])=[C:26](/[CH:27]=[CH:2]/[C:1]([C:4]4[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=4)=[O:3])[CH:29]=3)[N:21]=2)[CH2:15][CH2:16]1

참가 물질

5

반응물 3

HCID 740654-AcetylbenzenesulphonamideHCID 4177230Lithium methanolateHCID 178418754HCID 178418754, 화합물

생성물 1

HCID 178419032HCID 178419032, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-acetyl-benzenesulfonamide (Ex-26A, 0.12 g, 0.59 mmol) and 5-(2-cyclopropyl-1H-imidazol-4-yl)-2,4-dimethoxy-benzaldehyde (Ex-105B, 0.16 g, 0.59 mmol) in N,N-dimethylformamide (16 mL) was added lithium methoxide (1.0M in methanol, 2.4 mL, 2.4 mmol). The reaction mixture was allowed to stir for 18 hours at ambient temperature. The reaction was quenched with water. The aqueous solution was extracted with dichloromethane. The combined dichloromethane was concentrated. The crude product was purified by flash chromatography. Elution with methanol (10%, v/v, in dichloromethane) gave the title compound as red solid: m.p. 156–160° C. 1H NMR (DMSO-d6) δ 11.65 (bs, 1H), 8.32 (s, 1H), 8.19 (d, J=9.0 Hz, 2H), 8.00 (d, J=15.7 Hz, 1H), 7.95 (d, J=9.0 Hz, 2H), 7.62–7.52 (m, 2H), 7.24 (bs, 1H), 6.73 (s, 1H), 3.96 (s, 3H), 3.94 (s, 3H), 1.98–1.94 (m, 1H), 0.88–0.85 (m 4H). MS m/z=454 ([M+H]+, 100%).

후처리

  1. customThe reaction was quenched with water
  2. extractionThe aqueous solution was extracted with dichloromethane
  3. concentrationThe combined dichloromethane was concentrated
  4. customThe crude product was purified by flash chromatography
  5. washElution with methanol (10%, v/v, in dichloromethane)

출처 및 근거

ORD 기록
ord-bc0bededacff4f5c853c190677c0df9b
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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