Potassium Carbonate → methyl 2-((4-oxo-6-(4-(trifluoromethoxy)phenyl)quinazolin-3(4H)-yl)methyl)oxazole-4-carboxylate

HRID 1477222Notes

Reaction equation

HRID 1477222 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][NH:14][C:13]3=[O:20])=[CH:6][CH:5]=1.Cl[CH2:24][C:25]1[O:26][CH:27]=[C:28]([C:30]([O:32][CH3:33])=[O:31])[N:29]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.O.ClCCl>[O:20]=[C:13]1[C:12]2[C:17](=[CH:18][CH:19]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:21])[F:22])=[CH:5][CH:6]=3)[CH:11]=2)[N:16]=[CH:15][N:14]1[CH2:24][C:25]1[O:26][CH:27]=[C:28]([C:30]([O:32][CH3:33])=[O:31])[N:29]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2763199Methyl 2-(chloromethyl)oxazole-4-carboxylateHCID 1363523196-(4-(trifluoromethoxy)phenyl)quinazolin-4(3H)-one

Product 1

HCID 70974638methyl 2-((4-oxo-6-(4-(trifluoromethoxy)phenyl)quinazolin-3(4H)-yl)methyl)oxazole-4-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of 500 mg 6-(4-(trifluoromethoxy)phenyl)quinazolin-4(3H)-one, 340 mg of methyl 2-(chloromethyl)oxazole-4-carboxylate, and 220 mg potassium carbonate in 5 mL of DMA was heated at 80° C. for 16 h. The reaction was diluted with water and dichloromethane, aqueous layer washed with dichloromethane, combined organic layers dried over sodium sulphate and concentrated. The residue was recrystallized from acetonitrile to produce methyl 2-((4-oxo-6-(4-(trifluoromethoxy)phenyl)quinazolin-3(4H)-yl)methyl)oxazole-4-carboxylate Compound 177-A as a white solid (420 mg). MS m/z (ESI)=446.0 (base peak, M+H+); 891.1 (2M+H+); 913.1 (2M+Na+).

Workup

  1. washwashed with dichloromethane
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated
  4. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-73f0ea4046ed4015b9ae22a291d47953
Source dataset
uspto-grants-2016_08
Patent number
US09403782B2

Reaction notes

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