Water → HCID 136027561, compound

HRID 1428887Notes

Reaction equation

HRID 1428887 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][C:17]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:18][CH:19]=3)[N:14]=2)[CH:12]=1)=[O:7])C.O>C1COCC1>[O:23]=[C:21]1[C:20]2[C:15](=[CH:16][C:17]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:18][CH:19]=2)[N:14]=[C:13]([N:11]2[CH:12]=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=[N:10]2)[NH:22]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 136337191HCID 136337191, compound

Product 1

HCID 136027561HCID 136027561, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

Potassium hydroxide (37.4 mg, 0.666 mmol) was added to a mixture of 1-(4-oxo-7-phenyl-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (48.0 mg, 0.133 mmol), water (0.8 mL) and THF (0.8 mL). The mixture was stirred for 16 h at 23° C. The reaction mixture was concentrated under reduced pressure to remove the THF and the aqueous residue was acidified to pH 2 with 1M aq. HCl. The resulting precipitate was collected by filtration to provide the titled compound (42.0 mg, 85%). MS (ESI): mass calcd. for C18H12N4O3, 332.1; m/z found, 333.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 8.45 (d, J=0.8 Hz, 1H), 7.99 (d, J=8.2 Hz, 1H), 7.78-7.72 (m, 2H), 7.62 (d, J=1.5 Hz, 1H), 7.55 (d, J=0.8 Hz, 1H), 7.49 (t, J=7.6 Hz, 2H), 7.41-7.36 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove the THF
  3. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-36d2007acb37463aab8b2bd26b3c27cb
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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