Ethanol → 1-(1-oxo-1,2,7,8,9,10-hexahydro-benzo[f]quinazolin-3-yl)-1H-pyrazole-4-carboxylic acid

HRID 1428861Notes

Reaction equation

HRID 1428861 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:20](COCCOC)[C:19](=[O:27])[C:18]3[C:17]4[CH2:28][CH2:29][CH2:30][CH2:31][C:16]=4[CH:15]=[CH:14][C:13]=3[N:12]=2)[CH:10]=1)=[O:5])C.C(O)C>CCOCC>[O:27]=[C:19]1[C:18]2[C:17]3[CH2:28][CH2:29][CH2:30][CH2:31][C:16]=3[CH:15]=[CH:14][C:13]=2[N:12]=[C:11]([N:9]2[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]2)[NH:20]1

Participants

4

Reactant 2

HCID 702EthanolHCID 684861861-[2-(2-methoxy-ethoxymethyl)-1-oxo-1,2,7,8,9,10-hexahydro-benzo[f]quinazolin-3-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 1360276121-(1-oxo-1,2,7,8,9,10-hexahydro-benzo[f]quinazolin-3-yl)-1H-pyrazole-4-carboxylic acidYield 53.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Preparation of 1-(1-oxo-1,2,7,8,9,10-hexahydro-benzo[f]quinazolin-3-yl)-1H-pyrazole-4-carboxylic acid ethyl ester. HCl (4M in dioxane, 0.57 mL, 2.3 mmol) was added to a solution of 1-[2-(2-methoxy-ethoxymethyl)-1-oxo-1,2,7,8,9,10-hexahydro-benzo[f]quinazolin-3-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (70.0 mg, 0.164 mmol) and ethanol (0.57 mL). The reaction mixture was stirred at room temperature for 4 h, at which point ether (2 mL) was added and the precipitate was collected to yield the titled compound (27.0 mg, 49% yield). MS (ESI/Cl): mass calcd. for C18H18N4O3, 338.1; m/z found, 339.1 [M+H]+.

Workup

  1. additionwas added
  2. customthe precipitate was collected

Sources & evidence

ORD record
ord-7c7d997cd06c4ed1ad2725d6be5dc810
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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