Potassium Hydroxide → HCID 136027621, compound

HRID 1428845Notes

Reaction equation

HRID 1428845 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[NH:20][C:19](=[O:21])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH:22]4[CH2:24][CH2:23]4)[CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])C.[OH-].[K+]>C1COCC1>[CH:22]1([C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=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][C:19]3=[O:21])[CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 136337170HCID 136337170, compound

Product 1

HCID 136027621HCID 136027621, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(6-cyclopropyl-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (0.045 g, 0.139 mmol), 1M aq. KOH (0.694 mL) and THF (0.694 mL) was stirred for 18 h. The mixture was concentrated to remove the THF and the aqueous residue was acidified with 6 M aq. HCl at 0° C. The resulting precipitate was collected by filtration to provide the titled compound (0.035 g, 85%). MS (ESI/Cl): mass calcd. for C16H12N4O3, 296.1; m/z found, 297.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 12.92 (s, 2H), 8.93 (d, J=0.5 Hz, 1H), 8.24 (s, 1H), 7.81 (s, 1H), 7.65-7.50 (m, 2H), 2.22-2.04 (m, 1H), 1.14-0.94 (m, 2H), 0.85-0.68 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove the THF
  3. customwas acidified with 6 M aq. HCl at 0° C
  4. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-aa11025f13c04891a8b83e792c30cad8
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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