Dicyclohexylcarbodiimide → (S)-Tetrahydro-furan-3-carboxylic acid {4-[4-(diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-amide

HRID 1927597노트

반응식

HRID 1927597 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9]2)=[C:4]([F:28])[CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.[O:44]1[CH2:48][CH2:47][C@H:46]([C:49](O)=[O:50])[CH2:45]1>ClCCCl>[CH2:20]([N:17]([CH2:18][CH3:19])[C:15]([CH:14]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[N:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:49]([C@H:46]3[CH2:47][CH2:48][O:44][CH2:45]3)=[O:50])=[CH:3][C:4]=2[F:28])[CH2:9][CH2:10]1)=[O:16])[CH3:21]

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 40784874(3S)-oxolane-3-carboxylic acidHCID 581573072-[4-(4-amino-2-fluoro-phenyl)-piperazin-1-yl]-N,N-diethyl-2-phenyl-acetamide

생성물 1

HCID 58870766(S)-Tetrahydro-furan-3-carboxylic acid {4-[4-(diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-amide수율 51.1%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A mixture of 2-[4-(4-amino-2-fluoro-phenyl)-piperazin-1-yl]-N,N-diethyl-2-phenyl-acetamide (0.30 mmol) and DCC (1.0 mmol) in DCE (10 mL) was stirred at rt for 1 h, then was treated with (S)-tetrahydro-furan-3-carboxylic acid (1.0 mmol), and was stirred at rt for 16 h. The mixture was concentrated, and the residue was purified by PTLC to provide the title compound (74 mg, 51%). MS (ESI): mass calcd. for C27H35FN4O3, 482.27. m/z found, 483.4 [M+H]+. 1H NMR (CDCl3): 7.75-7.60 (m, 1H), 7.55-7.26 (m, 5H), 7.10-7.00 (m, 1H), 6.84 (t, J=9.0, 1H), 4.21 (s, 1H), 4.05-3.72 (m, 4H), 3.50-3.10 (m, 4H), 3.10-2.95 (m, 5H), 2.73-2.60 (m, 4H), 2.28-2.18 (m, 2H), 1.14-1.02 (m, 6H).

후처리

  1. stirringwas stirred at rt for 16 h
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by PTLC

출처 및 근거

ORD 기록
ord-d3fcf88553c545d5b90388f41f714809
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183239B2

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