Acetic Acid → 3-[(1,4-cis)-4-(4-Quinolin-5-yl-piperazin-1-yl)-cyclohexyl]-1H-indole-5-carbonitrile

HRID 992084

반응식

HRID 992084 반응식
[N:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[N:12]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:17]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2[CH:28]1[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1)#[N:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.Cl>ClC(Cl)C.CCOC(C)=O>[CH2:33]1[CH:28]([C:22]2[C:21]3[CH:20]=[C:19]([C:17]#[N:18])[CH:27]=[CH:26][C:25]=3[NH:24][CH:23]=2)[CH2:29][CH2:30][CH:31]([N:4]2[CH2:3][CH2:2][N:1]([C:7]3[C:8]4[CH:9]=[CH:10][CH:11]=[N:12][C:13]=4[CH:14]=[CH:15][CH:16]=3)[CH2:6][CH2:5]2)[CH2:32]1

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 106562265-(Piperazin-1-yl)quinolineHCID 112418863-(4-oxocyclohexyl)-1H-indole-5-carbonitrile

생성물 1

HCID 251412183-[(1,4-cis)-4-(4-Quinolin-5-yl-piperazin-1-yl)-cyclohexyl]-1H-indole-5-carbonitrile

시약·촉매·용매 2

HCID 63651,1-Dichloroethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 5-(1-piperazinyl)-quinoline (500 mg, 2.35 mmol), 4-(5-cyano-1H-3-indolyl)-cyclohexanone (540 mg, 2.35 mmol), and sodium triacetoxyborohydride (740 mg, 3.5 mmol) in dichloroethane (20 mL) was added acetic acid (0.27 mL, 4.7 mmol) and stirred overnight at room temperature. The reaction was quenched with 1 M NaOH (50 mL) and extracted in CH2Cl2 (3×100 mL). The organic fractions were combined, dried over Na2SO4, concentrated, filtered and chromatographed (5% MeOH/EtOAc) yielding 410 mg (41%) of the cis isomer as a white solid. The HCl salt was generated from EtOAc yielding a white solid: mp 220-223° C.

후처리

  1. customThe reaction was quenched with 1 M NaOH (50 mL)
  2. extractionextracted in CH2Cl2 (3×100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. filtrationfiltered
  6. customchromatographed (5% MeOH/EtOAc)
  7. customyielding 410 mg (41%) of the cis isomer as a white solid

출처 및 근거

ORD 기록
ord-76f5d489dff64744919f798fd553ebdb
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06465482B2

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