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

HRID 1876865Notes

Reaction equation

HRID 1876865 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)[CH:5]=[CH:4][N:3]=1.[NH2:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=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:22][C:23]3[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=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 866372883-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile

Product 1

HCID 580144184-(4-(1-(2-cyano-1-cyclopentylethyl)-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-cyclopentylpropanenitrile (500.0 mg, 0.001657 mol), p-aminobenzoic acid (341 mg, 0.00248 mol), and p-toluenesulfonic acid (240 mg, 0.0014 mol) in dry 1,4-dioxane (10 mL) was refluxed overnight. The mixture was cooled to room temperature. The resulting solid was filtered, washed with dioxane, and air dried to yield the desired product as a racemic mixture (460 mg, 69%). LCMS (M+H) 403.1.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe resulting solid was filtered
  3. washwashed with dioxane, and air
  4. customdried

Sources & evidence

ORD record
ord-9e97b91992924b43955ffdf369eb3ad1
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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