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Hydrochloric Acid → 1-(6-benzoylamino-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1428875
Notes
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Reaction equation

HRID 1428875 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 684879621-[6-benzoylamino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 1363371891-(6-benzoylamino-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent

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

  1. additionwas added
  2. customthe precipitate was collected

Sources & evidence

ORD record
ord-9a943ded5ce84826b3a060515a5cb894
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08937078B2

Reaction notes

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