Aluminium lithium hydride → 2,8-dimethyl-5-(2-(4-methylpiperazin-1-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 509845노트

반응식

HRID 509845 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]1[CH2:31][CH2:30][C:11]2[N:12]([CH2:20][C:21]([N:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)=O)[C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][C:18]=3[C:10]=2[CH2:9]1>C1COCC1>[CH3:7][N:8]1[CH2:31][CH2:30][C:11]2[N:12]([CH2:20][CH2:21][N:23]3[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]3)[C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][C:18]=3[C:10]=2[CH2:9]1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 578763372-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(4-methylpiperazin-1-yl)ethanone

생성물 1

HCID 578762952,8-dimethyl-5-(2-(4-methylpiperazin-1-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole수율 22.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

LAH (0.022 g, 0.58 mmol) was charged in dry THF (3 mL) and cooled to 0 deg C., 2-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(4-methylpiperazin-1-yl)ethanone (0.05 g, 0.147 mmol) was added to it portion wise. The reaction mixture was refluxed for 4 h. The reaction mixture was cooled to 0 deg C. and quenched with sat. Na2SO4. The solid formed was filtered through celite, washed with THF, dried over Na2SO4 and concentrated under reduced pressure to obtain 11 mg of 2,8-dimethyl-5-(2-(4-methylpiperazin-1-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole as TFA salt after purification by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 mL).

후처리

  1. temperaturecooled to 0 deg C
  2. temperatureThe reaction mixture was refluxed for 4 h
  3. temperatureThe reaction mixture was cooled to 0 deg C
  4. customand quenched with sat. Na2SO4
  5. customThe solid formed
  6. filtrationwas filtered through celite
  7. washwashed with THF
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5dc8f0a8c9ba48a6a88d8011fbc525e9
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096591B2

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