Water → 1-{4-[5-(2-Fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(pyridin-2-ylcarbamoyl)piperidine-4-carboxylic acid benzyl ester

HRID 2407514노트

반응식

HRID 2407514 반응식
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[CH2:15]([O:22][C:23]([C:25]1([C:56](Cl)=[O:57])[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[N:42]=[C:41]([C:43]4[CH:48]=[CH:47][C:46]([C:49]5[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=5)=[C:45]([F:55])[CH:44]=4)[O:40][N:39]=3)=[CH:34][CH:33]=2)[CH2:27][CH2:26]1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>ClCCl>[CH2:15]([O:22][C:23]([C:25]1([C:56](=[O:57])[NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:26][CH2:27][N:28]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[N:42]=[C:41]([C:43]4[CH:48]=[CH:47][C:46]([C:49]5[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=5)=[C:45]([F:55])[CH:44]=4)[O:40][N:39]=3)=[CH:34][CH:33]=2)[CH2:29][CH2:30]1)=[O:24])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 104392-AminopyridineHCID 866461104-Chlorocarbonyl-1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-piperidine-4-carboxylic acid benzyl ester

생성물 1

HCID 595094831-{4-[5-(2-Fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(pyridin-2-ylcarbamoyl)piperidine-4-carboxylic acid benzyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of triethyl amine (0.34 g, 0.0034 mol) in dichloromethane (20 mL), 2-amino pyridine (0.152 g, 0.0016 mol) is added. A solution of 4-chlorocarbonyl-1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-piperidine-4-carboxylic acid benzyl ester in dichloromethane (10 mL) is added slowly into the reaction mixture at 0-50 C. It is then stirred at room temperature for 1 hr. Demineralized water (15 mL) is added to the reaction mixture, organic layer is separated and the aqueous layer is extracted with (1×20 mL) dichloromethane. Combined organic layer is dried over sodium sulphate and concentrated under reduced pressure to get the crude material, which is purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate 60:40) to furnish 1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(pyridin-2-ylcarbamoyl)piperidine-4-carboxylic acid benzyl ester (138) (BS6.555).

후처리

  1. customis separated
  2. extractionthe aqueous layer is extracted with (1×20 mL) dichloromethane
  3. dry with materialCombined organic layer is dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto get the crude material, which
  6. customis purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate 60:40)

출처 및 근거

ORD 기록
ord-215867d475f642ea8300dd83c9d51665
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809539B2

반응 노트

불러오는 중…