p-Toluenesulfonic acid → HCID 58014495, compound

HRID 1876852Notes

Reaction equation

HRID 1876852 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]3([CH2:23][C:24]#[N:25])[CH2:16][N:15]([S:17]([CH:20]4[CH2:22][CH2:21]4)(=[O:19])=[O:18])[CH2:14]3)[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[N:26]1([C:31]2[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=2)[CH:30]=[CH:29][CH:28]=[N:27]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1.C(#N)C.O>[CH:20]1([S:17]([N:15]2[CH2:16][C:13]([CH2:23][C:24]#[N:25])([N:11]3[CH:12]=[C:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:35][C:34]5[CH:33]=[CH:32][C:31]([N:26]6[CH:30]=[CH:29][CH:28]=[N:27]6)=[CH:37][CH:36]=5)[N:7]=4)[CH:9]=[N:10]3)[CH2:14]2)(=[O:19])=[O:18])[CH2:22][CH2:21]1

Participants

7

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 5942744-(1H-Pyrazol-1-yl)anilineHCID 86637285HCID 86637285, compound

Product 1

HCID 58014495HCID 58014495, 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)-1-(cyclopropylsulfonyl)azetidin-3-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 (17.6 mg, 44%). LCMS (M+H) 502.0.

Workup

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

Sources & evidence

ORD record
ord-679d298b2c8141beba020c761acde823
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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