p-Toluenesulfonic acid → HCID 69032472, compound

HRID 1876843Notes

Reaction equation

HRID 1876843 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH:13]([CH2:17][CH:18]3[CH2:23][CH2:22][N:21]([C:24](=[O:33])[C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=4[F:32])[CH2:20][CH2:19]3)[CH2:14][C:15]#[N:16])[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[N:34]1([C:39]2[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][CH:40]=2)[CH:38]=[CH:37][N:36]=[CH:35]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1.C(#N)C.O>[N:34]1([C:39]2[CH:40]=[CH:41][C:42]([NH:43][C:2]3[N:7]=[C:6]([C:8]4[CH:9]=[N:10][N:11]([CH:13]([CH2:17][CH:18]5[CH2:23][CH2:22][N:21]([C:24](=[O:33])[C:25]6[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=6[F:32])[CH2:20][CH2:19]5)[CH2:14][C:15]#[N:16])[CH:12]=4)[CH:5]=[CH:4][N:3]=3)=[CH:44][CH:45]=2)[CH2:38][CH2:37][N:36]=[CH:35]1

Participants

7

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 3201654-(1H-imidazol-1-yl)anilineHCID 86637282HCID 86637282, compound

Product 1

HCID 69032472HCID 69032472, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-4-(1-(2,4-difluorobenzoyl)piperidin-4-yl)butanenitrile (30 mg, 0.06 mmol), 4-(1H-imidazol-1-yl)aniline (15.2 mg, 0.0956 mmol), and p-toluenesulfonic acid (9.3 mg, 0.054 mmol) in dry 1,4-dioxane (0.5 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 (25 mg, 71%). LCMS (M+H) 594.1.

Workup

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

Sources & evidence

ORD record
ord-cb4a3350a00543898e23b23029e7ae29
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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