Potassium Hydroxide → 1-(6-benzoylamino-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid
Reaction equation
[OH-].[K+].C([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([C:13]2[NH:22][C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([NH:24][C:25](=[O:32])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:19]=3)[N:14]=2)[CH:12]=1)=[O:7])C>C1COCC1>[C:25]([NH:24][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([N:11]1[CH:12]=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=[N:10]1)[NH:22][C:21]2=[O:23])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Aqueous 1M KOH (1.06 mL, 1.06 mmol) was added to 1-(6-benzoylamino-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (0.142 g, 0.343 mmol) in THF (1.0 mL). The reaction mixture was allowed to stir at room temperature for 18 h and was then concentrated. The residue was redissolved in water (5 mL) and brought to pH 1 with aqueous 1M HCl (3 mL). The resulting precipitate was collected by filtration to yield the titled compound (0.110 g, 82% yield). MS (ESI/Cl): mass calcd. for C19H13N5O4, 375.1; m/z found, 376.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 12.99 (s, 1H), 12.79 (s, 1H), 10.60 (s, 1H), 8.95 (s, 1H), 8.68 (s, 1H), 8.26 (s, 1H), 8.23 (dd, J=8.8, 2.4 Hz, 1H), 8.04-7.99 (m, 2H), 7.71 (d, J=7.8 Hz, 1H), 7.65-7.60 (m, 1H), 7.59-7.54 (m, 2H).
Workup
- concentrationwas then concentrated
- dissolutionThe residue was redissolved in water (5 mL)
- filtrationThe resulting precipitate was collected by filtration
Sources & evidence
- ORD record
- ord-a317e76490a34ee19515d804015955be
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937078B2
Reaction notes
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