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

HRID 1876888Notes

Reaction equation

HRID 1876888 reaction equation
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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6a8c111bd6fe4680b1f74623ef0e296a
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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