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

HRID 7625

Reaction equation

HRID 7625 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.NC1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:15]=1C(O)=O.[C:24]([OH:27])(=O)[CH3:25].C(N)=[NH:29].C[O:32][CH2:33][CH2:34]O>N>[F:23][C:21]1[CH:22]=[C:34]([CH:15]=[CH:19][CH:20]=1)[CH2:33][O:32][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[N:7]([CH2:25][C:24]([NH2:29])=[O:27])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 160693Formamidine acetateHCID 27249674-Fluoroanthranilic acidHCID 1353984967-Fluoroquinazolin-4(3H)-one

Product 1

HCID 98621802-[7-(3-Fluoro-benzyloxy)-4-oxo-4H-quinazolin-3-yl]-acetamideYield 81%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
130 °C

Procedure

7-Fluoro-3H-quinazolin-4-one: A mixture of 2-amino-4-fluorobenzoic acid (14.6 g, 94 mmol) and formamidine acetate (19.6 g, 18.8 mmol) in 2-methoxyethanol (110 mL) was heated at 130° C. for 18 h. After cooling, the mixture was half evaporated and an off-white solid formed. The mixture was diluted with ammonia (25%, 10 mL in 90 mL water) and the solid filtered off and washed with water. The solid was then washed with hexane and dried under high vacuum to afford the title compound (12.5 g, 81%) as an off-white solid. MS: m/e=165.2 (M+H+).

Workup

  1. temperatureAfter cooling
  2. customevaporated
  3. customan off-white solid formed
  4. filtrationthe solid filtered off
  5. washwashed with water
  6. washThe solid was then washed with hexane
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-7db9ee3861144166bfa97d305c987b83
Source dataset
uspto-grants-2006_08
Patent number
US07087612B2

Linked notes

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