1,2-Dichloroethane → (S)-3-(4-Fluorophenyl)-N-{1-[3-(4-pyridin-2-ylpiperazin-1-yl)phenyl]ethyl}-acrylamide

HRID 7593

반응식

HRID 7593 반응식
[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:26]=[C:27]([C@@H:31]([NH2:33])[CH3:32])[CH:28]=[CH:29][CH:30]=2)[CH2:21][CH2:20]1.C(Cl)CCl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([NH:33][C@H:31]([C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([N:22]3[CH2:21][CH2:20][N:19]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=4)[CH2:24][CH2:23]3)[CH:26]=2)[CH3:32])=[O:10])=[CH:11][CH:12]=1

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 980703-(4-Fluorophenyl)-2-propenoic acidHCID 58680156(S)-1-[3-(4-Pyridin-2-ylpiperazin-1-yl)phenyl]ethylamine

생성물 1

HCID 69591785(S)-3-(4-Fluorophenyl)-N-{1-[3-(4-pyridin-2-ylpiperazin-1-yl)phenyl]ethyl}-acrylamide수율 60.4%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

A solution of 4-fluorocinnamic acid (17 mg, 0.1 mmol), (S)-1-[3-(4-pyridin-2-yl-piperazin-1-yl)phenyl]ethylamine (24 mg, 0.11 mmol), EDC (28 mg, 0.15 mmol), DMAP (12 mg, 0.1 mmol) and triethylamine (40 mg, 0.4 mmol) in dichloromethane (2 ml) was stirred at room temperature for 14 h. The reaction mixture was purified by flash chromatography over silica gel with ethyl acetate/hexanes (1:1) to give the title compound as a solid (26 mg, 60% yield).

후처리

  1. customThe reaction mixture was purified by flash chromatography over silica gel with ethyl acetate/hexanes (1:1)

출처 및 근거

ORD 기록
ord-e9942dd2878d4dca917c28cc1fed1a55
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087609B2

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