Potassium Carbonate → HCID 136386245, compound

HRID 625775Notes

Reaction equation

HRID 625775 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[C:11]([NH:18][C:19](=O)[CH:20]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[OH:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CCO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:12]([C:13](=[O:14])[NH:15][C:19]([CH:20]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[OH:21])=[N:18]2)=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 66610642HCID 66610642, compound

Product 1

HCID 136386245HCID 136386245, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To 4-(benzyloxy)-2-(2-(4-fluorophenyl)-2-hydroxyacetamido)benzamide (4.1 g, 10.4 mmol) in absolute EtOH (50 mL) was added 20% aq potassium carbonate (5 mL). After heating and stirring at 80° C. for 20 h, the solution was cooled and concentrated to a solid. The solid was washed with water and dried under vacuum to afford 7-(benzyloxy)-2-((4-fluorophenyl)(hydroxy)methyl)quinazolin-4(3H)-one as a white solid (3.51 g, 90%). 1H NMR (300 MHz, DMSO-d6) δ ppm 5.25 (s, 2H) 5.55 (s, 1H) 7.10-7.21 (m, 4H) 7.36-7.48 (m, 5H) 7.56-7.61 (m, 2H) 7.97 (d, J=8.67 Hz, 1H). LC-MS (ESI) m/z 377 (M+H)+.

Workup

  1. temperatureAfter heating
  2. temperaturethe solution was cooled
  3. concentrationconcentrated to a solid
  4. washThe solid was washed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-74440d714ca34e1d942824cce72f2d2f
Source dataset
uspto-grants-2016_04
Patent number
US09308207B2

Reaction notes

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