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

HRID 428562ノート

反応式

HRID 428562 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 63651,1-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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 CH2Cl (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. Elemental Analysis for C28H29N5.HCl.1H2O; Calc'd C, 68.62; H, 6.58; N, 14.29; Found C, 68.99; H, 6.54; N, 14.06.

後処理

  1. customThe reaction was quenched with 1 M NaOH (50 mL)
  2. extractionextracted in CH2Cl (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

出典と根拠

ORDレコード
ord-a0cbd1b2e1e14e7eb536ceb47fa21a5c
出典データセット
uspto-grants-2001_11
特許番号
US06313126B1

反応ノート

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