3-((4-(hydroxymethyl)oxazol-2-yl)methyl)-6-(4-(trifluoromethoxy)phenyl)-2,3-dihydroquinazolin-4(1H)-one → 3-((4-(hydroxymethyl)oxazol-2-yl)methyl)-6-(4-(trifluoromethoxy)phenyl)quinazolin-4(3H)-one

HRID 517098Notes

Reaction equation

HRID 517098 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([CH2:8][N:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:20]4[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=4)[CH:16]=3)[NH:11][CH2:10]2)[O:6][CH:7]=1>C(OCC)(=O)C.[Pd]>[OH:1][CH2:2][C:3]1[N:4]=[C:5]([CH2:8][N:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:20]4[CH:21]=[CH:22][C:23]([O:26][C:27]([F:28])([F:30])[F:29])=[CH:24][CH:25]=4)[CH:16]=3)[N:11]=[CH:10]2)[O:6][CH:7]=1

Participants

4

Reactant 1

HCID 709746893-((4-(hydroxymethyl)oxazol-2-yl)methyl)-6-(4-(trifluoromethoxy)phenyl)-2,3-dihydroquinazolin-4(1H)-one

Product 1

HCID 709747523-((4-(hydroxymethyl)oxazol-2-yl)methyl)-6-(4-(trifluoromethoxy)phenyl)quinazolin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-((4-(Hydroxymethyl)oxazol-2-yl)methyl)-6-(4-(trifluoromethoxy)phenyl)-2,3-dihydroquinazolin-4(1H)-one Compound 177-B (120 mg) was stirred in ethyl acetate (20 mL) in the presence of palladium on carbon (10%, 120 mg) for 16 hours, then filtered through Celite® and purified by reverse-phase (ACN/H2O with 0.1% TFA) followed by neutralization on resin column to produce 44 mg of 3-((4-(hydroxymethyl)oxazol-2-yl)methyl)-6-(4-(trifluoromethoxy)phenyl)quinazolin-4(3H)-one Compound IV-24 as a white solid.

Workup

  1. filtrationfiltered through Celite®
  2. custompurified by reverse-phase (ACN/H2O with 0.1% TFA)

Sources & evidence

ORD record
ord-7b2502af8036438ea6ea3ba8b384a5b1
Source dataset
uspto-grants-2015_08
Patent number
US09115096B2

Reaction notes

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