p-Toluenesulfonic acid → 3-({4-[1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl]-5-methoxypyrimidin-2-yl}amino)benzoic Acid

HRID 1876899Notes

Reaction equation

HRID 1876899 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.[NH2:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([OH:28])=[O:27].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:20][CH3:21])=[CH:4][N:3]=[C:2]([NH:22][C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=3)[C:26]([OH:28])=[O:27])[N:7]=2)[CH:9]=[N:10]1)[CH:17]1[CH2:19][CH2:18]1)#[N:16]

Participants

5

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 74193-Aminobenzoic AcidHCID 312751,4-DioxaneHCID 866373033-[4-(2-chloro-5-methoxypyrimidin-4-yl)-1H-pyrazol-1-yl]-3-cyclopropylpropanenitrile

Product 1

HCID 687585973-({4-[1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl]-5-methoxypyrimidin-2-yl}amino)benzoic AcidYield 99.5%

Procedure

A mixture of 3-[4-(2-chloro-5-methoxypyrimidin-4-yl)-1H-pyrazol-1-yl]-3-cyclopropylpropanenitrile (from example 320 step 1, 250 mg, 0.00082 mol), 3-aminobenzoic acid (169 mg, 0.00123 mol), and p-toluenesulfonic acid (120 mg, 0.00070 mol) in dry 1,4-dioxane (5 mL, 0.07 mol) was refluxed overnight, then cooled to room temperature. The insoluble material was filtered off. The filtration was evaporated to dryness to give the crude product (330 mg, 99.14%). LCMS (M+H) 405.3.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe insoluble material was filtered off
  3. filtrationThe filtration
  4. customwas evaporated to dryness

Sources & evidence

ORD record
ord-eb2c412ba356472892584b8af705e02d
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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