Cesium carbonate → 5-Chloro-2-methoxy-N-(2-(1-(3-isopropylthioureidosulfonyl)piperidin-4-yl)ethyl)benzamide

HRID 2043075ノート

反応式

HRID 2043075 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([S:18]([NH2:21])(=[O:20])=[O:19])[CH2:14][CH2:13]1)=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].[CH:31]([N:34]=[C:35]=[S:36])([CH3:33])[CH3:32]>CN1CCCC1=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([S:18]([NH:21][C:35]([NH:34][CH:31]([CH3:33])[CH3:32])=[S:36])(=[O:20])=[O:19])[CH2:14][CH2:13]1)=[O:8]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 75263Isopropyl IsothiocyanateHCID 122820304-(2-(5-Chloro-2-methoxybenzamido)ethyl)piperidine-1-sulfonamide

生成物 1

HCID 115185565-Chloro-2-methoxy-N-(2-(1-(3-isopropylthioureidosulfonyl)piperidin-4-yl)ethyl)benzamide収率 60%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

188 mg (0.5 mmol) of 4-(2-(5-chloro-2-methoxybenzamido)ethyl)piperidine-1-sulfonamide and 326 mg (1 mmol) of cesium carbonate were heated in 5 ml of N-methyl-2-pyrrolidone with 0.1 ml (0.9 mmol) of isopropyl isothiocyanate at 80° C. for 10 minutes. The reaction mixture was poured onto ice/2 M hydrochloric acid and extracted three times with 10 ml of dichloromethane each time. The combined organic phases were dried over sodium sulfate and filtered after addition of activated carbon. The crude product obtained after removal of the solvent was recrystallized from methanol. 142 mg (60%) of the title compound were obtained as a colorless solid.

後処理

  1. additionThe reaction mixture was poured onto ice/2 M hydrochloric acid
  2. extractionextracted three times with 10 ml of dichloromethane each time
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. additionafter addition of activated carbon
  6. customThe crude product obtained
  7. customafter removal of the solvent
  8. customwas recrystallized from methanol

出典と根拠

ORDレコード
ord-d9484b6b11754664b874ae0ba8078f6f
出典データセット
uspto-grants-2013_11
特許番号
US08586612B2

反応ノート

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