4-Aminobenzoic Acid → 4-(4-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)pyrimidin-2-ylamino)benzoic Acid

HRID 1876883

Reaction equation

HRID 1876883 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)[CH:5]=[CH:4][N:3]=1.[NH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=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[CH:5]=[CH:4][N:3]=[C:2]([NH:20][C:21]3[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=3)[N:7]=2)[CH:9]=[N:10]1)[CH:17]1[CH2:19][CH2:18]1)#[N:16]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 6101p-Toluenesulfonic acidHCID 866372933-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopropylpropanenitrile

Product 1

HCID 580144544-(4-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)pyrimidin-2-ylamino)benzoic Acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopropylpropanenitrile (2.74 g, 0.0100 mol), p-aminobenzoic acid (2.06 g, 0.0150 mol), and p-toluenesulfonic acid (1.5 g, 0.0085 mol) in dry 1,4-dioxane (80 mL) was refluxed overnight. The mixture was cooled to room temperature, filtered. The solid was washed with dioxane, air dried to yield the desired product as a racemic mixture (3.02 g, 80.58%). LCMS (M+H) 375.3.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationfiltered
  3. washThe solid was washed with dioxane, air
  4. customdried

Sources & evidence

ORD record
ord-26f869aef9204275bb308e478280a5aa
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Linked notes

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