Hydrochloric Acid → methyl {(3S)-1-[5-(adamantan-1-ylcarbamoyl)-6-(propylthio)pyridin-2-yl]piperidin-3-yl}acetate

HRID 2424916ノート

反応式

HRID 2424916 の反応式
[C:1]12([NH:11][C:12](=[O:24])[C:13]3[CH:18]=[CH:17][C:16](Cl)=[N:15][C:14]=3[S:20][CH2:21][CH2:22][CH3:23])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH:25]1[CH2:30][CH2:29][CH2:28][C@@H:27]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH2:26]1.Cl.C(=O)([O-])[O-].[K+].[K+]>C(#N)CCC.CCOC(C)=O>[C:1]12([NH:11][C:12]([C:13]3[CH:18]=[CH:17][C:16]([N:25]4[CH2:30][CH2:29][CH2:28][C@@H:27]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH2:26]4)=[N:15][C:14]=3[S:20][CH2:21][CH2:22][CH3:23])=[O:24])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 40153895methyl 2-[(3S)-piperidin-3-yl]acetateHCID 59830706N-adamantan-1-yl-6-chloro-2-(propylthio)nicotinamide

生成物 1

HCID 59830770methyl {(3S)-1-[5-(adamantan-1-ylcarbamoyl)-6-(propylthio)pyridin-2-yl]piperidin-3-yl}acetate収率 44%

試薬・触媒・溶媒 2

HCID 8008Butyronitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

N-adamantan-1-yl-6-chloro-2-(propylthio)nicotinamide (0.365 g, 1 mmol) was added to (S)-methyl 2-(piperidin-3-yl)acetate.HCl (0.194 g, 1 mmol) and potassium carbonate (0.415 g, 3 mmol) in butyronitrile (4 mL) was heated at 150° C. for 2 hours. The reaction mixture was diluted with EtOAc (50 mL), and washed sequentially with water (20 mL) and brine (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in hexane. Pure fractions were evaporated to dryness to afford methyl {(3S)-1-[5-(adamantan-1-ylcarbamoyl)-6-(propylthio)pyridin-2-yl]piperidin-3-yl}acetate (0.215 g, 44%) as a white solid.

後処理

  1. washwashed sequentially with water (20 mL) and brine (20 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product
  6. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in hexane
  7. customPure fractions were evaporated to dryness

出典と根拠

ORDレコード
ord-80e4e4eb1cc34be293daeb5729fa15b2
出典データセット
uspto-grants-2011_06
特許番号
US07964618B2

反応ノート

読み込み中…