Water → 1-(1-oxo-1,2,7,8,9,10-hexahydro-benzo[f]quinazolin-3-yl)-1H-pyrazole-4-carboxylic acid
Reaction equation
O.[OH-].[Li+].O.C([O:7][C:8]([C:10]1[CH:11]=[N:12][N:13]([C:15]2[NH:24][C:23](=[O:25])[C:22]3[C:21]4[CH2:26][CH2:27][CH2:28][CH2:29][C:20]=4[CH:19]=[CH:18][C:17]=3[N:16]=2)[CH:14]=1)=[O:9])C>C1COCC1>[O:25]=[C:23]1[C:22]2[C:21]3[CH2:26][CH2:27][CH2:28][CH2:29][C:20]=3[CH:19]=[CH:18][C:17]=2[N:16]=[C:15]([N:13]2[CH:14]=[C:10]([C:8]([OH:9])=[O:7])[CH:11]=[N:12]2)[NH:24]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Lithium hydroxide monohydrate (9.3 mg, 0.22 mmol) and water (0.19 mL) were added to 1-(1-oxo-1,2,7,8,9,10-hexahydro-benzo[f]quinazolin-3-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (25.0 mg, 73.9 pmol) in THF (0.28 mL). The reaction mixture was stirred at room temperature for 18 h and was then concentrated. The residue was redissolved in water (3 mL) and this solution was brought to pH 1 with 1M aqueous HCl. The resulting precipitate was collected and dried to yield the titled compound (19.6 mg, 85% yield). MS (ESI/Cl): mass calcd. for C16H14N4O3, 310.1; m/z found, 311.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 12.98 (s, 1H), 12.42 (s, 1H), 8.92 (s, 1H), 8.23 (s, 1H), 7.51 (d, J=8.5 Hz, 1H), 7.41 (d, J=8.3 Hz, 1H), 3.37 (t, J=5.8 Hz, 2H), 2.83 (t, J=5.3 Hz, 2H), 1.84-1.67 (m, 4H).
Workup
- concentrationwas then concentrated
- dissolutionThe residue was redissolved in water (3 mL)
- customThe resulting precipitate was collected
- customdried
Sources & evidence
- ORD record
- ord-2018445f6e6d4e4e8f8fd745189f0051
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937078B2
Reaction notes
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