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

反応式

HRID 490631 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-20fa11b5f5c245a69a21324fefbe55a4
出典データセット
uspto-grants-2009_05
特許番号
US07528136B2

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