Potassium Hydroxide → HCID 135860564, compound

HRID 1428825Notes

Reaction equation

HRID 1428825 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]([O:22][C:23]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH:26]=[CH:25][CH:24]=4)[CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])C.[OH-].[K+]>C1COCC1>[C:23]1([O:22][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])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 136337161HCID 136337161, compound

Product 1

HCID 135860564HCID 135860564, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-[6-(naphthalen-1-yloxy)-4-oxo-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.42 g, 0.99 mmol), 1M aq. KOH (5.0 mL) and THF (5.0 mL) was stirred for 4 h. The mixture was concentrated 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 (0.34 g, 86%). MS (ESI): mass calcd. for C22H14N4O4, 398.1; m/z found, 399.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 12.99 (s, 1H), 12.86 (s, 1H), 8.94 (s, 1H), 8.24 (s, 1H), 8.06 (d, J=8.1 Hz, 1H), 8.02 (d, J=8.3 Hz, 1H), 7.87 (d, J=8.2 Hz, 1H), 7.78 (d, J=8.2 Hz, 1H), 7.71 (dd, J=8.9, 2.9 Hz, 1H), 7.62 (t, J=7.5 Hz, 1H), 7.60-7.54 (m, 2H), 7.38 (s, 1H), 7.24 (d, J=7.4 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-4041c72f6eeb40848372630168958b9a
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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