p-Toluenesulfonic acid → 3-cyclopropyl-3-(4-{5-methoxy-2-[(3-nitrophenyl)amino]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile

HRID 1876898Notes

Reaction equation

HRID 1876898 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH:13]([CH:17]3[CH2:19][CH2:18]3)[CH2:14][C:15]#[N:16])[CH:12]=2)[C:5]([O:20][CH3:21])=[CH:4][N:3]=1.[N+:22]([C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=1)[NH2:28])([O-:24])=[O:23].C1(C)C=CC(S(O)(=O)=O)=CC=1.O1CCOCC1>C(#N)C.O>[CH:17]1([CH:13]([N:11]2[CH:12]=[C:8]([C:6]3[C:5]([O:20][CH3:21])=[CH:4][N:3]=[C:2]([NH:28][C:27]4[CH:29]=[CH:30][CH:31]=[C:25]([N+:22]([O-:24])=[O:23])[CH:26]=4)[N:7]=3)[CH:9]=[N:10]2)[CH2:14][C:15]#[N:16])[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 74233-NitroanilineHCID 312751,4-DioxaneHCID 866373033-[4-(2-chloro-5-methoxypyrimidin-4-yl)-1H-pyrazol-1-yl]-3-cyclopropylpropanenitrile

Product 1

HCID 580145013-cyclopropyl-3-(4-{5-methoxy-2-[(3-nitrophenyl)amino]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of a mixture of 3-[4-(2-chloro-5-methoxypyrimidin-4-yl)-1H-pyrazol-1-yl]-3-cyclopropylpropanenitrile (from example 320 step 1, 60 mg, 0.0002 mol), m-nitroaniline (40.9 mg, 0.000296 mol), and p-toluenesulfonic acid (29 mg, 0.00017 mol) in dry 1,4-dioxane (1 mL, 0.02 mol) was refluxed overnight. The mixture was diluted with acetonitrile and water, purified on RP-HPLC at pH 10 to give the desired product as a racemic mixture (free base). LCMS (M+H) 406.2.

Workup

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

Sources & evidence

ORD record
ord-0f6384c5713d47f5968c53ac63982cba
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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