Piperidin-4-ol → N-Cyclopropyl-N-{1-[3-(4-hydroxy-piperidin-1-yl)-propionyl]-piperidin-4-yl}-3-trifluoromethyl-benzenesulfonamide

HRID 1428954노트

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HRID 1428954 반응식
[C:1]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH:25]2[CH2:27][CH2:26]2)[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)(=[O:14])=[O:13])[CH2:7][CH2:6]1)(=[O:4])[CH:2]=[CH2:3].[OH:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>>[CH:25]1([N:11]([CH:8]2[CH2:7][CH2:6][N:5]([C:1](=[O:4])[CH2:2][CH2:3][N:32]3[CH2:33][CH2:34][CH:29]([OH:28])[CH2:30][CH2:31]3)[CH2:10][CH2:9]2)[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:22])[F:24])[CH:16]=2)(=[O:13])=[O:14])[CH2:26][CH2:27]1

참가 물질

3

반응물 2

HCID 79341Piperidin-4-olHCID 58002117N-(1-Acryloyl-piperidin-4-yl)-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide

생성물 1

HCID 24860750N-Cyclopropyl-N-{1-[3-(4-hydroxy-piperidin-1-yl)-propionyl]-piperidin-4-yl}-3-trifluoromethyl-benzenesulfonamide

반응 조건

온도
150 °C

실험 절차

N-(1-Acryloyl-piperidin-4-yl)-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide (1) (125 mg, 0.31 mmol), 4-hydroxypiperidine (313 mg, 3.1 mmol) and ETOH (2.5 ml) were mixed together in a sealed tube and heated to 150° C. with microwave equipment for 30 min. After the reaction, the reaction mixture was evaporated in vacuum and the residue was purified by column chromatography on silica gel (CHCl3/MeOH/NH3 aq.=100/10/1) to afford the desired compound as free base, which was dissolved in AcOEt (2 ml), and treated with 4N—HCl in AcOEt (2 ml) solution. The resulting mixture was concentrated in vacuo, and dried under reduced pressure for 24 hours at 60° C. to afford the title compound 2 as a HCl-salt (white amorphous, 151 mg, yield 90%) LC: 100%. MS: m/z=503.8, 504.49 (M+H+).

후처리

  1. customAfter the reaction
  2. customthe reaction mixture was evaporated in vacuum
  3. customthe residue was purified by column chromatography on silica gel (CHCl3/MeOH/NH3 aq.=100/10/1)

출처 및 근거

ORD 기록
ord-1d6aee9fc9444a378dbd5eaf346cfd30
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937181B2

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