Hydrochloric Acid → 1-(6-benzoylamino-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester
Reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1[CH:8]=[N:9][N:10]([C:12]2[N:21](COCC[Si](C)(C)C)[C:20](=[O:30])[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH:31][C:32](=[O:39])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH:18]=3)[N:13]=2)[CH:11]=1)=[O:6])[CH3:3].O1CCOCC1>CCOCC>[CH2:2]([O:4][C:5]([C:7]1[CH:8]=[N:9][N:10]([C:12]2[NH:21][C:20](=[O:30])[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH:31][C:32](=[O:39])[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:18]=3)[N:13]=2)[CH:11]=1)=[O:6])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Hydrochloric acid (4M in dioxane, 2.0 mL, 8.0 mmol) was added to a solution of 1-[6-benzoylamino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.239 g, 0.488 mmol) and dioxane (2.0 mL). The reaction mixture was stirred at room temperature for 18 h, at which point ether (10 mL) was added and the precipitate was collected to yield the titled compound (0.157 g, 86% yield). MS (ESI/Cl): mass calcd. for C21H17N5O4, 403.1; m/z found, 404.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 12.87 (s, 1H), 10.62 (s, 1H), 9.01 (s, 1H), 8.69 (s, 1H), 8.32 (s, 1H), 8.23 (dd, J=8.9, 2.4 Hz, 1H), 8.06-7.96 (m, 2H), 7.84-7.49 (m, 4H), 4.31 (q, J=7.1 Hz, 2H), 1.33 (t, J=7.1 Hz, 3H).
Workup
- additionwas added
- customthe precipitate was collected
Sources & evidence
- ORD record
- ord-9a943ded5ce84826b3a060515a5cb894
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937078B2
Reaction notes
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