Ethyl 4-fluoro-3-chlorobenzimidate → 2-[2-(3-chloro-4-fluorophenyl)-6-hydroxy-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide

HRID 1157438Notes

Reaction equation

HRID 1157438 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][C:8](=[O:13])[NH:9][CH:10]([CH3:12])[CH3:11])=[O:5].[F:19][C:20]1[CH:30]=[CH:29][C:23]([C:24](=N)OCC)=[CH:22][C:21]=1[Cl:31]>C(O)C>[Cl:31][C:21]1[CH:22]=[C:23]([C:24]2[N:6]([CH2:7][C:8]([NH:9][CH:10]([CH3:12])[CH3:11])=[O:13])[C:4](=[O:5])[C:3]3[C:2](=[CH:17][CH:16]=[C:15]([OH:18])[CH:14]=3)[N:1]=2)[CH:29]=[CH:30][C:20]=1[F:19]

Participants

4

Reactant 2

HCID 2730158Ethyl 4-fluoro-3-chlorobenzimidateHCID 59511750HCID 59511750, compound

Product 1

HCID 595117832-[2-(3-chloro-4-fluorophenyl)-6-hydroxy-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamideYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-5-hydroxy-N-(isopropylcarbamoylmethyl)benzamide (INTERMEDIATE II.1) (400 mg, 1.59 mmol) and ethyl 4-fluoro-3-chlorobenzimidate*HCl (INTERMEDIATE III.5) (1.14 g, 4.78 mmol) in ethanol (10 mL) was heated at reflux temperature for 1 h. The mixture was then cooled to room temperature and the resultant solid collected by filtration and washed with additional portions of cold ethanol (3×20 mL) to afford 2-[2-(3-chloro-4-fluorophenyl)-6-hydroxy-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide (INTERMEDIATE IV.1) (380 mg, 0.97 mmol, 61%) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 h
  3. filtrationthe resultant solid collected by filtration
  4. washwashed with additional portions of cold ethanol (3×20 mL)

Sources & evidence

ORD record
ord-9ff401797e7a4c13a60272c4ce353923
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

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