Ethanolamine → N-(2-Hydroxy-ethyl)-3-{4-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonamide

HRID 1928407노트

반응식

HRID 1928407 반응식
[CH2:1]([CH2:3][NH2:4])[OH:2].C(N(CC)CC)C.Cl.[F:13][C:14]([F:48])([F:47])[C:15]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[N:18]=[C:17]([C:31]2[CH:36]=[CH:35][N:34]=[C:33]([C:37]3[CH:38]=[C:39]([S:43](Cl)(=[O:45])=[O:44])[CH:40]=[CH:41][CH:42]=3)[CH:32]=2)[N:16]=1>C1COCC1>[OH:2][CH2:1][CH2:3][NH:4][S:43]([C:39]1[CH:40]=[CH:41][CH:42]=[C:37]([C:33]2[CH:32]=[C:31]([C:17]3[N:16]=[C:15]([C:14]([F:13])([F:47])[F:48])[CH:20]=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:23][CH:22]=4)[N:18]=3)[CH:36]=[CH:35][N:34]=2)[CH:38]=1)(=[O:44])=[O:45]

참가 물질

5

반응물 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 60209344HCID 60209344, 화합물

생성물 1

HCID 57469057N-(2-Hydroxy-ethyl)-3-{4-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonamide수율 76.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a cooled (ice-water bath) and stirred mixture of ethanolamine (0.066 g, 1.08 mmol), triethylamine (0.11 ml, 0.76 mmol) and THF (2 ml) was added drop wise a solution of 3-{4-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonyl chloride hydrochloride (example I.1) (0.21 g, 0.36 mmol) in THF (3 ml). The mixture was allowed to stir at room temperature for 16 h. Purification of the reaction mixture by flash chromatography on silica gel (ethyl acetate/hexane) and crystallization (diethyl ether/hexane) yielded the title compound as a white solid (0.156 g, 76%). MS (ISP) 569.2 [(M+H)+]; mp 192.5° C.

후처리

  1. stirringto stir at room temperature for 16 h
  2. customPurification of the reaction mixture by flash chromatography
  3. customon silica gel (ethyl acetate/hexane) and crystallization (diethyl ether/hexane)

출처 및 근거

ORD 기록
ord-fcbb34c9e66f47a8b284bd7334b1012c
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183262B2

반응 노트

불러오는 중…