2-Chlorobenzenesulfonyl chloride → N-Biphenyl-4-yl-3-[4-(2-chloro-benzenesulfonyl)-piperazin-1-yl]-3-oxo-propionamide

HRID 1665609노트

반응식

HRID 1665609 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].Cl.[C:13]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:30])[CH2:21][C:22](=[O:29])[N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C>ClCCl>[C:13]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:30])[CH2:21][C:22]([N:23]2[CH2:24][CH2:25][N:26]([S:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])(=[O:10])=[O:9])[CH2:27][CH2:28]2)=[O:29])=[CH:17][CH:18]=1

참가 물질

5

반응물 3

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66625265N-Biphenyl-4-yl-3-oxo-3-piperazin-1-yl-propionamide hydrochloride

생성물 1

HCID 44231085N-Biphenyl-4-yl-3-[4-(2-chloro-benzenesulfonyl)-piperazin-1-yl]-3-oxo-propionamide수율 36%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-Chlorobenzenesulfonyl chloride (35.4 mg, 0.17 mmol) was added at 0° C. to a stirred solution of N-biphenyl-4-yl-3-oxo-3-piperazin-1-yl-propionamide hydrochloride (60 mg, 0.17 mmol) and DIEA (24.6 mg, 0.19 mmol) in dichloromethane (2 mL). the resulting mixture was stirred for 2 hrs then the product was extracted with dichloromethane. The organics was separated and washed with saturated sodium bicarbonate solution, followed by brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by column chromatography using silica gel 60-120 mesh with 60% ethyl acetate in hexane as eluant to afford 30 mg (36%) of N-Biphenyl-4-yl-3-[4-(2-chloro-benzenesulfonyl)-piperazin-1-yl]-3-oxo-propionamide. LCMS: 498.12 (M+1)+ 96.7%. 1H NMR: (CDCl3): δ 9.6 (s, 1H), 8.06 (d, 1H), 7.56 (m, 8H), 7.42 (t, 3H), 7.34 (t, 1H), 3.78 (t, 2H), 3.7 (t, 2H), 3.48 (s, 2H), 3.38 (m, 4H).

후처리

  1. extractionthe product was extracted with dichloromethane
  2. customThe organics was separated
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-e86b2dcca6ca4833b52596a19fce67f9
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039463B2

반응 노트

불러오는 중…