1-(3-(Trifluoromethyl)phenyl)piperazine → [(2S,4S)-1-Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidin-2-yl]-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

HRID 490631

반응식

HRID 490631 반응식
[CH2:1]([N:8]1[CH2:12][CH:11]([NH:13][CH2:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[CH2:10][CH:9]1[C:29]([OH:31])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[F:54][C:55]([F:69])([F:68])[C:56]1[CH:57]=[C:58]([N:62]2[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]2)[CH:59]=[CH:60][CH:61]=1>ClCCl.C(N(CC)CC)C>[CH2:1]([N:8]1[CH2:12][C@@H:11]([NH:13][CH2:14][C:15]2[CH:16]=[C:17]([C:25]([F:28])([F:26])[F:27])[CH:18]=[C:19]([C:21]([F:23])([F:22])[F:24])[CH:20]=2)[CH2:10][C@H:9]1[C:29]([N:65]1[CH2:64][CH2:63][N:62]([C:58]2[CH:59]=[CH:60][CH:61]=[C:56]([C:55]([F:68])([F:69])[F:54])[CH:57]=2)[CH2:67][CH2:66]1)=[O:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866253011-Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid

생성물 1

HCID 86625302[(2S,4S)-1-Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidin-2-yl]-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone수율 10.6%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

The mixture of 1-benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid (65 mg, 0.146 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (54.5.0 mg, 0.292 mmol), N-hydroxybenzotriazole (20.7 mg, 0.146 mmol), and 1-(3-trifluoromethyl-phenyl)-piperazine (29.67 mg, 0.219 mmol), triethylamine (0.08 ml) in dry dichloromethane (2 mL) was stirred overnight, and then concentrated. The residue was purified by preparative HPLC on reversed phase eluting with an acetonitrile/water [0.1% aq NH3 (25%)] gradient to afford the title compound (10.2 mg, 10.6%) as a light yellow oil. MS m/e=659.4 [M+H]+.

후처리

  1. concentrationconcentrated
  2. customThe residue was purified by preparative HPLC on reversed phase
  3. washeluting with an acetonitrile/water [0.1% aq NH3 (25%)] gradient

출처 및 근거

ORD 기록
ord-20fa11b5f5c245a69a21324fefbe55a4
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528136B2

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