Potassium Hydroxide → HCID 135895253, compound

HRID 1428830Notes

Reaction equation

HRID 1428830 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[NH:20][C:19](=[O:21])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[CH3:28])[CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])C.[OH-].[K+]>C1COCC1>[O:21]=[C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])[CH:17]=2)[N:12]=[C:11]([N:9]2[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]2)[NH:20]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 136337162HCID 136337162, compound

Product 1

HCID 135895253HCID 135895253, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4-oxo-6-o-tolyl-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (40.0 mg, 1.07 mmol), 1M aq. KOH (0.5 mL) and THF (1 mL) was stirred for 16 h. The reaction mixture was concentrated under reduced pressure to remove the THF and the aqueous residue was acidified to pH 2 with 1 M aq. HCl. The resulting precipitate was collected by filtration to provide the titled compound (30.0 mg, 81%). MS (ESI): mass calcd. for C19H14N4O3, 346.1; m/z found 347.0 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 13.04 (s, 1H), 12.93 (s, 1H), 8.99 (s, 1H), 8.28 (s, 1H), 8.02 (s, 1H), 7.86 (d, J=7.5 Hz, 1H), 7.76 (d, J=7.8 Hz, 1H), 7.37-7.29 (m, 4H), 2.28 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove the THF
  3. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-3b64d7d1127d4dc984cdde1c51e67dd6
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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