4-Aminobenzoic Acid → 4-(4-(1-(2-cyano-1-cyclopentylethyl)-1H-pyrazol-4-yl)-5-methoxypyrimidin-2-ylamino)benzoic Acid

HRID 1876885Notes

Reaction equation

HRID 1876885 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH:13]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:14][C:15]#[N:16])[CH:12]=2)[C:5]([O:22][CH3:23])=[CH:4][N:3]=1.[NH2:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[C:15]([CH2:14][CH:13]([N:11]1[CH:12]=[C:8]([C:6]2[C:5]([O:22][CH3:23])=[CH:4][N:3]=[C:2]([NH:24][C:25]3[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=3)[N:7]=2)[CH:9]=[N:10]1)[CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)#[N:16]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 6101p-Toluenesulfonic acidHCID 866372913-(4-(2-chloro-5-methoxypyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile

Product 1

HCID 580145474-(4-(1-(2-cyano-1-cyclopentylethyl)-1H-pyrazol-4-yl)-5-methoxypyrimidin-2-ylamino)benzoic Acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(4-(2-chloro-5-methoxypyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile (120 mg, 0.36 mmol), p-aminobenzoic acid (74.4 mg, 0.542 mmol), and p-toluenesulfonic acid (53 mg, 0.31 mmol) in dry 1,4-dioxane (3 mL) was refluxed overnight. The mixture was cooled to room temperature. The resulting solid was filtered and washed with dioxane to give the desired product as a racemic mixture (120 mg, 76.7%). LCMS (M+H) 433.3.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe resulting solid was filtered
  3. washwashed with dioxane

Sources & evidence

ORD record
ord-c618cc0da1f74a0cb29e53a12a1e8aa7
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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