p-Toluenesulfonic acid → 3-cyclopentyl-3-(4-(2-(4-(4-(methylsulfonyl)piperazin-1-yl)phenylamino)pyrimidin-4-yl)-1H-pyrazol-1-yl)propanenitrile

HRID 1876858ノート

反応式

HRID 1876858 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH:13]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:14][C:15]#[N:16])[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[N:22]1([C:28]2[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=2)[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C1(C)C=C[C:38]([S:41](O)(=[O:43])=[O:42])=CC=1.C(=O)([O-])[O-].[Na+].[Na+].CS(Cl)(=O)=O>O1CCOCC1.O>[CH:17]1([CH:13]([N:11]2[CH:12]=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:32][C:31]4[CH:33]=[CH:34][C:28]([N:22]5[CH2:23][CH2:24][N:25]([S:41]([CH3:38])(=[O:43])=[O:42])[CH2:26][CH2:27]5)=[CH:29][CH:30]=4)[N:7]=3)[CH:9]=[N:10]2)[CH2:14][C:15]#[N:16])[CH2:21][CH2:20][CH2:19][CH2:18]1

参加物

8

反応物 5

HCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 4229251-(4-Aminophenyl)piperazineHCID 866372883-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile

生成物 1

HCID 580146523-cyclopentyl-3-(4-(2-(4-(4-(methylsulfonyl)piperazin-1-yl)phenylamino)pyrimidin-4-yl)-1H-pyrazol-1-yl)propanenitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 3-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile (30 mg, 0.1 mmol), 4-(piperazin-1-yl)aniline (28.5 mg, 0.149 mmol), and p-toluenesulfonic acid (14 mg, 0.084 mmol) in dry 1,4-dioxane (0.8 mL) was refluxed overnight, then cooled to room temperature. To the resulting mixture was added 1.0 M sodium carbonate in water (0.8 mL), followed by methanesulfonyl chloride (0.015 mL, 0.20 mmol). The reaction was stirred at room temperature for 30 min and the phases were separated. The organic phase was purified on RP-HPLC at pH 10 to give the desired product as a racemic mixture (33 mg, 63%). LCMS (M+H) 521.1.

後処理

  1. temperaturewas refluxed overnight
  2. customthe phases were separated
  3. customThe organic phase was purified on RP-HPLC at pH 10

出典と根拠

ORDレコード
ord-77d16fafda214554ab5b38a1dfce2400
出典データセット
uspto-grants-2012_11
特許番号
US08309718B2

反応ノート

読み込み中…