p-Toluenesulfonic acid → 1-(isoxazol-5-ylcarbonyl)-4-(4-(2-(4-(1H-pyrazol-1-yl)phenyl)aminopyrimidin-4-yl)-1H-pyrazol-1-yl)piperidin-4-ylacetonitrile

HRID 1876848Notes

Reaction equation

HRID 1876848 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]3([CH2:26][C:27]#[N:28])[CH2:18][CH2:17][N:16]([C:19]([C:21]4[O:25][N:24]=[CH:23][CH:22]=4)=[O:20])[CH2:15][CH2:14]3)[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[N:29]1([C:34]2[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=2)[CH:33]=[CH:32][CH:31]=[N:30]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1.C(#N)C.O>[O:25]1[C:21]([C:19]([N:16]2[CH2:17][CH2:18][C:13]([CH2:26][C:27]#[N:28])([N:11]3[CH:12]=[C:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:38][C:37]5[CH:36]=[CH:35][C:34]([N:29]6[CH:33]=[CH:32][CH:31]=[N:30]6)=[CH:40][CH:39]=5)[N:7]=4)[CH:9]=[N:10]3)[CH2:14][CH2:15]2)=[O:20])=[CH:22][CH:23]=[N:24]1

Participants

7

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 5942744-(1H-Pyrazol-1-yl)anilineHCID 86637284(4-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-1-(isoxazol-5-ylcarbonyl)piperidin-4-yl)acetonitrile

Product 1

HCID 580145321-(isoxazol-5-ylcarbonyl)-4-(4-(2-(4-(1H-pyrazol-1-yl)phenyl)aminopyrimidin-4-yl)-1H-pyrazol-1-yl)piperidin-4-ylacetonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of (4-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-1-(isoxazol-5-ylcarbonyl)piperidin-4-yl)acetonitrile (30 mg, 0.08 mmol), 4-(1H-pyrazol-1-yl)aniline (18.9 mg, 0.119 mmol), and p-toluenesulfonic acid (12 mg, 0.067 mmol) in dry 1,4-dioxane (0.6 mL) was refluxed overnight. The mixture was diluted with acetonitrile and water, purified on RP-HPLC to give the desired product as a racemic mixture (22 mg, 52%). LCMS (M+H) 521.1.

Workup

  1. temperaturewas refluxed overnight
  2. custompurified on RP-HPLC

Sources & evidence

ORD record
ord-f8f71fbfa1804b8a81976b67d7d88f5f
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

Loading…