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Ethanol → 2-(4-(4-((6-Amino-5-fluoro-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol

HRID 1972644
ノート
印刷プレビュー

反応式

HRID 1972644 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH:13]([C:33]#[C:34][CH3:35])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:36].[OH-].[NH4+:38].CCO>O>[NH2:38][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH:13]([C:33]#[C:34][CH3:35])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:36]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 702EthanolHCID 14923Ammonium HydroxideHCID 866704242-(4-(4-((6-Chloro-5-fluoro-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol

生成物 1

HCID 866704252-(4-(4-((6-Amino-5-fluoro-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol収率 37%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
150 °C

実験手順

A 20-mL microwave vial was charged with 2-(4-(4-((6-chloro-5-fluoro-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (165 mg, 0.30 mmol), aq. ammonium hydroxide (3 mL, 30% solution, 15.4 mmol, J. T. Baker, Phillipsburg, N.J.) and EtOH (3 mL). The is reaction vessel was sealed and the mixture heated to 150° C. overnight. The reaction was diluted with water (50 mL) and extracted with EtOAc (3×100 mL). The combined organics were dried (Na2SO4), filtered, and concentrated to give an oil that was purified via column chromatography on silica gel (0-10% MeOH in CH2Cl2) to give 2-(4-(4-((6-amino-5-fluoro-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (60 mg) as a mixture of two isomers.

後処理

  1. customThe is reaction vessel
  2. customwas sealed
  3. extractionextracted with EtOAc (3×100 mL)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil that
  8. customwas purified via column chromatography on silica gel (0-10% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-9b2375d3974143dd81afea5f6446cc8c
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08431563B2

反応ノート

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