Acetic Acid → 3-cyclopentyl-3-[4-(2-{[4-(2-pyrrolidin-1-ylethoxy)phenyl]amino}pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile

HRID 1876888ノート

反応式

HRID 1876888 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([CH2:27][CH2:28][O:29][C:30]2[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1.C(O)(=O)C>>[CH:17]1([CH:13]([N:11]2[CH:12]=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:34][C:33]4[CH:35]=[CH:36][C:30]([O:29][CH2:28][CH2:27][N:22]5[CH2:26][CH2:25][CH2:24][CH2:23]5)=[CH:31][CH:32]=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

4

反応物 3

HCID 176Acetic AcidHCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)anilineHCID 866372883-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile

生成物 1

HCID 580145133-cyclopentyl-3-[4-(2-{[4-(2-pyrrolidin-1-ylethoxy)phenyl]amino}pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile

実験手順

A mixture of 3-[4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl]-3-cyclopentylpropanenitrile (prepared according to the procedure described in Example 33, Step 2; 0.030 g, 0.000099 mol) and 4-(2-pyrrolidin-1-ylethoxy)aniline (0.0308 g, 0.000149 mol) in acetic acid (0.7 mL, 0.01 mol) was refluxed overnight. After being evaporated to dryness, the residue was diluted with EtOAc, washed with aqueous sodium bicarbonate, brine, dried, and concentrated. The residue was applied on RP-HPLC to obtain the desired product as a racemic mixture (free base). LCMS (M+H) 472.4.

後処理

  1. customprepared
  2. customAfter being evaporated to dryness
  3. additionthe residue was diluted with EtOAc
  4. washwashed with aqueous sodium bicarbonate, brine
  5. customdried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-6a8c111bd6fe4680b1f74623ef0e296a
出典データセット
uspto-grants-2012_11
特許番号
US08309718B2

反応ノート

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