4-Aminobenzoic Acid → HCID 67376481, compound

HRID 1876884Notes

Reaction equation

HRID 1876884 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]3([CH2:19][C:20]#[N:21])[CH2:16][CH:15]([C:17]#[N:18])[CH2:14]3)[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:17]([CH:15]1[CH2:16][C:13]([N:11]2[CH:12]=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:22][C:23]4[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=4)[N:7]=3)[CH:9]=[N:10]2)([CH2:19][C:20]#[N:21])[CH2:14]1)#[N:18]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 6101p-Toluenesulfonic acidHCID 86637301HCID 86637301, compound

Product 1

HCID 67376481HCID 67376481, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-3-(cyanomethyl)-cyclobutanecarbonitrile (300 mg, 0.00100 mol), p-aminobenzoic acid (206 mg, 0.00151 mol), and p-toluenesulfonic acid (150 mg, 0.00085 mol) in dry 1,4-dioxane (8 mL) was refluxed overnight, cooled to room temperature. The solid was filtered and collected to give the titled compound as a cis- and trans-isomer mixture, which was used directly in next step (310 mg, 77.3%). LCMS (M+H) 400.4.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe solid was filtered
  3. customcollected

Sources & evidence

ORD record
ord-74ca97f00c4947e08120a2d0eb16189a
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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