Diisopropylethylamine → t-Butyl 4-(3-(1-phenylethylamino)-4-(2,2,2-trifluoroacetyl) phenyl)piperazine-1-carboxylate

HRID 1910541노트

반응식

HRID 1910541 반응식
[C:1]1([CH:7]([NH:9][C:10]2[CH:15]=[C:14](F)[CH:13]=[CH:12][C:11]=2[C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:23]1([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(N(CC)C(C)C)(C)C>C(#N)C>[C:1]1([CH:7]([NH:9][C:10]2[CH:15]=[C:14]([N:26]3[CH2:25][CH2:24][N:23]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:28][CH2:27]3)[CH:13]=[CH:12][C:11]=2[C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 587072761-(2-(1-Phenylethylamino)-4-fluorophenyl)-2,2,2-trifluoroethanone

생성물 1

HCID 58707346t-Butyl 4-(3-(1-phenylethylamino)-4-(2,2,2-trifluoroacetyl) phenyl)piperazine-1-carboxylate수율 30.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1-(2-(1-Phenylethylamino)-4-fluorophenyl)-2,2,2-trifluoroethanone (150 mg, 0.48 mmol), t-butyl piperazine-1-carboxylate (98.7 mg, 0.53 mmol), N,N-diisopropylethylamine (124 mg, 0.96 mmol) were stirred at 80° C. in dry acetonitrile (25 mL) for 21 h. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated and the crude compound was purified by silica chromatography using 25% ethyl acetate in hexanes to afford the title compound (70 mg, 30% yield). 1H NMR (400 MHz, CDCl3): δ 9.36 (d, 1H), 7.60 (d, 1H), 7.32 (m, 4H), 7.24 (m, 1H), 6.13 (d, 1H), 5.61 (s, 1H), 4.55 (m, 1H), 3.41 (m, 4H), 3.25 (m, 2H), 3.14 (m, 2H), 1.61 (d, 3H), 1.46 (s, 9H); MS (ESI) m/z: Calculated for C25H30F3N3O3: 477.22; Observed: 500.3 (M++Na).

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated
  5. customthe crude compound was purified by silica chromatography

출처 및 근거

ORD 기록
ord-d9fc396eabb441e4a9772f2a8b9352bb
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604021B2

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