Water → HCID 67398853, 화합물

HRID 70620노트

반응식

HRID 70620 반응식
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[Cl:6][C:7]1[C:8]([O:30][CH3:31])=[N:9][C:10]([C:13]([C:20]2[CH:25]=[CH:24][C:23]([S:26][CH:27]3[CH2:29][CH2:28]3)=[CH:22][CH:21]=2)=[CH:14][C@H:15]2[CH2:19][CH2:18][NH:17][CH2:16]2)=[CH:11][CH:12]=1.C(N(CC)CC)C.O>O1CCCC1>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:20]2[CH:21]=[CH:22][C:23]([S:26][CH:27]3[CH2:28][CH2:29]3)=[CH:24][CH:25]=2)=[CH:14][C@H:15]2[CH2:19][CH2:18][N:17]([C:1](=[O:4])[CH2:2][CH3:3])[CH2:16]2)=[N:9][C:8]=1[O:30][CH3:31]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 673995383-chloro-6-{1-[4-(cyclopropylsulfanyl)phenyl]-2-[(3R)-pyrrolidin-3-yl]ethenyl}-2-methoxypyridine

생성물 1

HCID 67398853HCID 67398853, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Propionyl chloride (58 μL) was added to a solution of 3-chloro-6-{1-[4-(cyclopropylsulfanyl)phenyl]-2-[(3R)-pyrrolidin-3-yl]ethenyl}-2-methoxypyridine (EZ mixture) (235 mg) and triethylamine (83 μL) in tetrahydrofuran (6 mL) under ice-cooling, and the mixture was stirred at room temperature for four hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:5) to give 1-[(3R)-3-{2-(5-chloro-6-methoxypyridin-2-yl)-2-[4-(cyclopropylsulfanyl)phenyl]ethenyl}pyrrolidin-1-yl]propan-1-one (EZ mixture) as a crude product (363 mg).

후처리

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customafter which the solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:5)

출처 및 근거

ORD 기록
ord-693fde58721a4844a1da8607afd13633
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822503B2

반응 노트

불러오는 중…