Potassium Hydroxide → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-(2-pyrimidinylthio) butyramide

HRID 52076

反応式

HRID 52076 の反応式
[SH:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-].[K+].[N:10]1([CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([O:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][NH:28][C:29](=[O:34])[CH2:30][CH2:31][CH2:32]Cl)[CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>CO>[N:10]1([CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([O:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][NH:28][C:29](=[O:34])[CH2:30][CH2:31][CH2:32][S:1][C:2]3[N:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

参加物

5

反応物 3

HCID 14797Potassium HydroxideHCID 67726214N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-chlorobutyramideHCID 178418793HCID 178418793、化合物

生成物 1

HCID 44211247N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-(2-pyrimidinylthio) butyramide収率 92.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

2.78 g of 2-mercaptopyrimidine were added to a solution of 1.95 g of 85% potassium hydroxide and 9.03 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-chlorobutyramide (prepared as described in Preparation 2) in 140 ml of methanol, and the resulting mixture was heated under reflux for 15 hours. At the end of this time, the reaction mixture was cooled, and the solvent was removed by distillation under reduced pressure. The resulting residue was mixed with water, and the aqueous mixture was extracted with ethyl acetate. The extract was concentrated by evaporation under reduced pressure, and the concentrate was purified by column chromatography through silica gel, using a 9:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 10.1 g (yield 92%) of the title compound as an oil.

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 15 hours
  3. temperatureAt the end of this time, the reaction mixture was cooled
  4. customthe solvent was removed by distillation under reduced pressure
  5. additionThe resulting residue was mixed with water
  6. extractionthe aqueous mixture was extracted with ethyl acetate
  7. concentrationThe extract was concentrated by evaporation under reduced pressure
  8. customthe concentrate was purified by column chromatography through silica gel
  9. additionby volume mixture of ethyl acetate and methanol as the eluent

出典と根拠

ORDレコード
ord-6720e96c746444a589f225034fd47ddf
出典データセット
uspto-grants-1997_04
特許番号
US05616579

関連ノート

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