Ammonium Hydroxide → 2-(2-(4-((6-Amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol

HRID 1972646ノート

反応式

HRID 1972646 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[N:22]=[CH:21][C:20]([C:23]([OH:29])([CH3:28])[C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=3)[CH:13]([C:30]#[C:31][CH3:32])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[NH4+:34]>CCO>[NH2:34][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][C:20]([C:23]([OH:29])([CH3:28])[C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=3)[CH:13]([C:30]#[C:31][CH3:32])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 14923Ammonium HydroxideHCID 866704262-(2-(4-((6-Chloro-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol

生成物 1

HCID 569329932-(2-(4-((6-Amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol収率 79.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
120 °C

実験手順

To a 330-mL pressure vessel was added 2-(2-(4-((6-chloro-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol (6.50 g, 13.3 mmol), EtOH (80 mL), and ammonium hydroxide (30%, 80.0 mL, 616 mmol, J. T. Baker, Philipsburg, N.J.). The tube was sealed and heated at 120° C. for 10 h and then the solvent was removed in vacuo. The residue was partitioned between water (100 mL) and DCM (200 mL). The aqueous layer was extracted with DCM (2×100 mL) and the combined organic extracts were dried over MgSO4, filtered, and concentrated. The crude product was purified by column chromatography (330 g of silica, 1 to 5% 2 M NH3 in MeOH in DCM) to afford 2-(2-(4-((6-amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol (5.0 g) as a mixture of four isomers.

後処理

  1. customThe tube was sealed
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between water (100 mL) and DCM (200 mL)
  4. extractionThe aqueous layer was extracted with DCM (2×100 mL)
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (330 g of silica, 1 to 5% 2 M NH3 in MeOH in DCM)

出典と根拠

ORDレコード
ord-2066f7965b4f476eb6eb310f9879acb2
出典データセット
uspto-grants-2013_04
特許番号
US08431563B2

反応ノート

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