Water → HCID 67398853、化合物

HRID 70620ノート

反応式

HRID 70620 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 67398853HCID 67398853、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-693fde58721a4844a1da8607afd13633
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

反応ノート

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