4-Aminobenzoic Acid → HCID 68754988, compound

HRID 1876894Notes

Reaction equation

HRID 1876894 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH:13]([CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH2:14][C:15]#[N:16])[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[NH2:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=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:23][C:24]3[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=3)[N:7]=2)[CH:9]=[N:10]1)[CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)#[N:16]

Participants

5

Reactant 4

HCID 9784-Aminobenzoic AcidHCID 6101p-Toluenesulfonic acidHCID 312751,4-DioxaneHCID 86637302HCID 86637302, compound

Product 1

HCID 68754988HCID 68754988, compound

Procedure

A mixture of 3-[4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl]-3-(tetrahydro-2H-pyran-4-yl)propanenitrile (from example 308 step 3, 140 mg, 0.00044 mol), p-aminobenzoic acid (90.6 mg, 0.000661 mol), and p-toluenesulfonic acid (64 mg, 0.00037 mol) in dry 1,4-dioxane (3 mL, 0.04 mol) was refluxed overnight, cooled to room temperature. The desired product crashed out and was collected by filtration (180 mg, 97.64%). LCMS (M+H) 419.3.

Workup

  1. temperaturewas refluxed overnight

Sources & evidence

ORD record
ord-83bf6ee3c31443fa8ac99c87478ff18e
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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