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Hydrochloric Acid → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-methoxyacetamidoquinazoline hydrochloride

HRID 634737
Notes
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Reaction equation

HRID 634737 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:28]=[C:27]([CH3:29])[C:26]([O:30]C(OC)=O)=[CH:25][C:5]=1[NH:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([NH:19][C:20](=[O:24])[CH2:21][O:22][CH3:23])=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]=[CH:9][N:8]=1.[ClH:35]>CO.O>[ClH:35].[F:3][C:4]1[CH:28]=[C:27]([CH3:29])[C:26]([OH:30])=[CH:25][C:5]=1[NH:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([NH:19][C:20](=[O:24])[CH2:21][O:22][CH3:23])=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]=[CH:9][N:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 107894254-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxy-7-methoxyacetamidoquinazoline

Product 1

HCID 212602834-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-methoxyacetamidoquinazoline hydrochlorideYield 82%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Procedure

2M Aqueous sodium hydroxide solution (620 μl) was added dropwise to a suspension of 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxy-7-methoxyacetamidoquinazoline (275 mg, 0.62 mmol) in methanol (8 ml) at 5° C. and the mixture then stirred for 90 minutes at ambient temperature. The reaction mixture was diluted with water and adjusted to pH7 with 2M hydrochloric acid. The precipitated solid was collected by filtration, resuspended in ethanol and a 5M solution of hydrogen chloride in isopropanol (0.3 ml) added. The volatiles were removed from the resulting solution by evaporation and the solid washed with ether collected by filtration and dried under vacuum to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-methoxyacetamidoquinazoline hydrochloride (216 mg, 82%).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. additiona 5M solution of hydrogen chloride in isopropanol (0.3 ml) added
  3. customThe volatiles were removed from the resulting solution by evaporation
  4. washthe solid washed with ether
  5. filtrationcollected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c83a28a9c46640a182e3a9bcaa415882
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06184225B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes