Ethanol → N-(7-methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-isobutyramide

HRID 545506노트

반응식

HRID 545506 반응식
C(Cl)(=O)C.C(O)C.Cl.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([NH:17]N)[CH:14]=[CH:15][CH:16]=1.O=[C:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[CH2:22][CH2:21]1>C(OCC)(=O)C>[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:14]([C:21]3[CH2:22][CH:23]([NH:26][C:27](=[O:31])[CH:28]([CH3:29])[CH3:30])[CH2:24][CH2:25][C:20]=3[NH:17]2)=[CH:15][CH:16]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 6367Acetyl chlorideHCID 27239403-Methoxyphenylhydrazine hydrochlorideHCID 215339942-Methyl-N-(4-oxocyclohexyl)propanamide

생성물 1

HCID 59161215N-(7-methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-isobutyramide수율 31.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Follow the procedures essentially as described in Preparation 6, above, using acetyl chloride (26 mL, 360 mmol) and absolute ethanol (90 mL) with 3-methoxyphenylhydrazine hydrochloride (5.24 g, 30 mmol) and N-(4-oxo-cyclohexyl)-isobutyramide (5.50 g, 30 mmol). When complete, dilute the reaction with ethyl acetate (200 mL) and wash with 0.5N NaOH and sodium bicarbonate solution. Filter the solids in the organic phase, triturate in dichloromethane and filter to give 2.67 g (31%) gray solid. MS (ES): m/z 287 (M+1), 285 (M−1); 1H NMR(DMSO-d6): δ 10.52 (s, 1H), 7.83 (d, 1H, J=7.5 Hz), 7.21 (d, 1H, J=8.4 Hz), 6.78 (s, 1H), 6.60 (d, 1H, J=8.4 Hz), 4.00 (m, 1H), 3.75 (s, 3H), 2.87 (dd, 1H, J=14.8, 5.1 Hz), 2.76 (m, 2H), 2.48-2.36 (m, 2H), 2.48-2.36 (m, 2H), 1.76 (m, 1H), 1.03 (d, 6H, J=6.6 Hz).

후처리

  1. customas described in Preparation 6
  2. additionWhen complete, dilute
  3. washwash with 0.5N NaOH and sodium bicarbonate solution
  4. filtrationFilter the solids in the organic phase
  5. customtriturate in dichloromethane
  6. filtrationfilter

출처 및 근거

ORD 기록
ord-8f72a4b9037442e9b4f7ba28d4052d7b
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935722B2

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