5-Amino-4-fluoro-2-methylphenyl Methoxyformate → 7-Benzyloxy-4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)quinazoline hydrochloride

HRID 279639Notes

Reaction equation

HRID 279639 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:6]([O:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:3]=1[NH2:4].Cl.[CH2:16]([O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([Cl:34])=[N:29][CH:30]=[N:31]2)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(O)CCC>[ClH:34].[CH2:16]([O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([NH:4][C:3]3[CH:5]=[C:6]([O:10][C:11]([O:13][CH3:14])=[O:12])[C:7]([CH3:9])=[CH:8][C:2]=3[F:1])=[N:29][CH:30]=[N:31]2)=[CH:26][CH:25]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 226250465-Amino-4-fluoro-2-methylphenyl MethoxyformateHCID 226250837-Benzyloxy4-chloroquinazoline hydrochloride

Product 1

HCID 226249607-Benzyloxy-4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)quinazoline hydrochlorideYield 97%

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Procedure

2-Fluoro-5-methoxycarbonyloxy-4-methylaniline (883 mg, 4.4 mmol), (prepared as described for the starting material in Example 12), was added to a solution of 7-benzyloxy-4-chloroquinazoline hydrochloride(1 g, 3.7 mmol) in 2-pentanol (15 ml) at 120° C. and the mixture was then heated at reflux for 4 hours. The mixture was allowed to cool and the precipitate was collected by filtration, washed with isopropanol followed by ether and dried under vacuum to give 7-benzyloxy-4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)quinazoline hydrochloride (1.65 g, 97%) as a cream solid.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureat reflux for 4 hours
  3. temperatureto cool
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with isopropanol
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c55e61c3c6e04642876c8b54030bf043
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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