Sodium Methoxide → 2-[7-(3-Fluoro-benzyloxy)-2-methyl-4-oxo-4H-quinazolin-3-yl]-acetamide

HRID 7630

Reaction equation

HRID 7630 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:18])[NH:12][C:13]([CH3:17])=[N:14]2)=[CH:9][CH:8]=1.NC1C=C(OCC2C=CC=C(F)C=2)C=CC=1C(O)=O.CCO[C:44]([C:46]([NH2:48])=[O:47])=O.Cl.C[O-].[Na+]>CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:18])[N:12]([CH2:44][C:46]([NH2:48])=[O:47])[C:13]([CH3:17])=[N:14]2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 10942334Sodium Methoxide2×HCID 19983589Ethyl acetamidate hydrochloride2×HCID 21991777HCID 21991777, compoundHCID 1357527147-(3-Fluoro-benzyloxy)-2-methyl-3h-quinazolin-4-one

Product 1

HCID 100201802-[7-(3-Fluoro-benzyloxy)-2-methyl-4-oxo-4H-quinazolin-3-yl]-acetamideYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

7-(3-Fluoro-benzyloxy)-2-methyl-3H-quinazolin-4-one: To a mixture of 2-amino-4-(3-fluoro-benzyloxy)-benzoic acid (2.0 g, 7.7 mmol) and ethyl acetamidate HCl (1.9 g, 15.3 mmol) in methanol (30 mL) was added sodium methoxide (5.4 M, 0.83 g, 15.3 mmol) and the resulting mixture was heated under reflux for 19 h. After this time ethyl acetamidate HCl (1.9 g, 15.3 mmol) and sodium methoxide (5.4 M, 0.83 g, 15.3 mmol) was added and the resulting mixture heated for another 1 h. After cooling to rt the mixture was poured into water (40 mL) and then the resulting precipitate was stirred for 2 h, and filtered off to afford the title compound (2.1 g, 97%) as an off-white solid. MS: m/e=283.1 (M−H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 19 h
  3. temperaturethe resulting mixture heated for another 1 h
  4. filtrationfiltered off

Sources & evidence

ORD record
ord-b61c6f8fbaaa4529848801b75a7c15ca
Source dataset
uspto-grants-2006_08
Patent number
US07087612B2

Linked notes

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