p-Toluenesulfonic acid → HCID 58014460, compound

HRID 1876893Notes

Reaction equation

HRID 1876893 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH:13]([CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH2:14][C:15]#[N:16])[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[N:23]1([C:29]2[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O1CCOCC1>C(#N)C.O>[N:23]1([C:29]2[CH:30]=[CH:31][C:32]([NH:33][C:2]3[N:7]=[C:6]([C:8]4[CH:9]=[N:10][N:11]([CH:13]([CH:17]5[CH2:22][CH2:21][O:20][CH2:19][CH2:18]5)[CH2:14][C:15]#[N:16])[CH:12]=4)[CH:5]=[CH:4][N:3]=3)=[CH:34][CH:35]=2)[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 312751,4-DioxaneHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 86637302HCID 86637302, compound

Product 1

HCID 58014460HCID 58014460, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-[4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl]-3-(tetrahydro-2H-pyran-4-yl)propanenitrile (20 mg, 0.00008 mol), 4-morpholin-4-ylaniline (20.1 mg, 0.000113 mol), and p-toluenesulfonic acid (11 mg, 0.000064 mol) in dry 1,4-dioxane (0.5 mL, 0.006 mol) was refluxed overnight. The mixture was diluted with acetonitrile and water, purified on RP-HPLC at pH 10 to provide the desired product as a racemic mixture (free base). LCMS (M+H) 460.4.

Workup

  1. temperaturewas refluxed overnight
  2. custompurified on RP-HPLC at pH 10

Sources & evidence

ORD record
ord-d0af02a4366940e1b20417db92530828
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

Loading…