Triethylamine → 2-(4-(4-((2,6-Dichloropyridin-3-yl)sulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol

HRID 1972537노트

반응식

HRID 1972537 반응식
Cl.Cl.[F:3][C:4]([F:24])([F:23])[C:5]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1)([OH:10])[C:6]([F:9])([F:8])[F:7].C(N(CC)CC)C.[Cl:32][C:33]1[C:38]([S:39](Cl)(=[O:41])=[O:40])=[CH:37][CH:36]=[C:35]([Cl:43])[N:34]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:32][C:33]1[C:38]([S:39]([N:20]2[CH2:21][CH2:22][N:17]([C:14]3[CH:13]=[CH:12][C:11]([C:5]([OH:10])([C:6]([F:9])([F:8])[F:7])[C:4]([F:3])([F:23])[F:24])=[CH:16][CH:15]=3)[CH2:18][CH2:19]2)(=[O:41])=[O:40])=[CH:37][CH:36]=[C:35]([Cl:43])[N:34]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 193787122,6-Dichloropyridine-3-sulfonyl chlorideHCID 866703461,1,1,3,3,3-Hexafluoro-2-(4-(1-piperazinyl)phenyl)-2-propanol dihydrochloride

생성물 1

HCID 866703912-(4-(4-((2,6-Dichloropyridin-3-yl)sulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol수율 79.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a 20-mL vial was added 1,1,1,3,3,3-hexafluoro-2-(4-(1-piperazinyl)phenyl)-2-propanol dihydrochloride (0.40 g, 1.0 mmol, Example 91), CH2Cl2 (8 mL), and triethylamine (0.70 mL, 5.0 mmol). To this solution was added 2,6-dichloropyridine-3-sulfonyl chloride (0.30 g, 1.2 mmol, Organic Process Research and Development 2009, 875). After stirring overnight at room temperature, saturated aqueous sodium bicarbonate and CH2Cl2 were added to the reaction mixture. After stirring for 5 min, the solution was transferred onto a phase separation cartridge (Radleys Discovery Technologies, Essex, UK) with the organic phase being collected and passed through a plug of Na2SO4. The collected solution was purified by silica gel chromatography (0 to 70% EtOAc in hexanes) to afford 2-(4-(4-((2,6-dichloropyridin-3-yl)sulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (0.43 g) as an off-white solid.

후처리

  1. stirringAfter stirring for 5 min
  2. customthe solution was transferred onto a phase separation cartridge (Radleys Discovery Technologies, Essex, UK) with the organic phase
  3. custombeing collected
  4. customThe collected solution was purified by silica gel chromatography (0 to 70% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-d3a99f362fe942928d63f51df28559ef
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431563B2

반응 노트

불러오는 중…