Potassium Hydroxide → HCID 135860562, compound

HRID 1428823Notes

Reaction equation

HRID 1428823 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][C:15]([CH3:31])=[C:16]([O:22][C:23]4[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=4[CH3:30])[CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])C.[OH-].[K+]>C1COCC1>[CH3:29][C:28]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:30])[C:23]=1[O:22][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[CH3:31])[N:12]=[C:11]([N:9]1[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]1)[NH:20][C:19]2=[O:21]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 136337160HCID 136337160, compound

Product 1

HCID 135860562HCID 135860562, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-[6-(2,6-dimethyl-phenoxy)-7-methyl-4-oxo-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.25 g, 0.60 mmol), 1M aq. KOH (5.0 mL) and THF (5.0 mL) was stirred for 4 h. The mixture was concentrated to remove the THF and the aqueous residue was acidified to pH 2 with 1M aq. HCl. The resulting precipitate was collected by filtration to provide the titled compound (0.22 g, 93%). MS (ESI): mass calcd. for C21H18N4O4, 390.1; m/z found, 391.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 12.99 (s, 1H), 12.72 (s, 1H), 8.90 (d, J=13.2 Hz, 1H), 8.22 (s, 1H), 7.68 (s, 1H), 7.25 (d, J=7.4 Hz, 2H), 7.18 (dd, J=8.3, 6.7 Hz, 1H), 6.78 (s, 1H), 2.55 (s, 3H), 2.07 (d, J=8.2 Hz, 6H).

Workup

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

Sources & evidence

ORD record
ord-7e0b8f8afc5449fe82b38801ea45c2b2
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

Loading…