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Hydrochloric Acid → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline hydrochloride

HRID 1737518
Notes
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Reaction equation

HRID 1737518 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:30]=[C:29]([CH3:31])[C:28]([O:32]C(OC)=O)=[CH:27][C:5]=1[NH:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][N:22]3[CH:26]=[CH:25][N:24]=[CH:23]3)=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]=[CH:9][N:8]=1.O.[ClH:38]>CO>[ClH:38].[F:3][C:4]1[CH:30]=[C:29]([CH3:31])[C:28]([OH:32])=[CH:27][C:5]=1[NH:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][N:22]3[CH:26]=[CH:25][N:24]=[CH:23]3)=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]=[CH:9][N:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 226250254-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline

Product 1

HCID 226250234-(2-Fluoro-5-hydroxy-4-methylanilino)-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline hydrochlorideYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

2M Aqueous sodium hydroxide (0.3ml , 6 mmol) was added to a solution of 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline (257 mg, 5.5 mmol) in methanol (5 ml) and the mixture stirred for 1 hour at 40° C. Water and 1M hydrochloric acid (0.6 ml) were added and the mixture concentrated to half volume by evaporation. The resulting solid was collected by filtration, dissolved in methylene chloride/methanol and a solution of 7M hydrogen chloride in isopropanol (0.4 ml) was added. The volatiles were removed by evaporation, the solid residue was triturated with ether, collected by filtration and dried under vacuum to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline hydrochloride (160 mg, 60%).

Workup

  1. concentrationthe mixture concentrated to half volume by evaporation
  2. filtrationThe resulting solid was collected by filtration
  3. dissolutiondissolved in methylene chloride/methanol
  4. additiona solution of 7M hydrogen chloride in isopropanol (0.4 ml) was added
  5. customThe volatiles were removed by evaporation
  6. customthe solid residue was triturated with ether
  7. filtrationcollected by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-30fffc87c6cb4553b327f6e2fab7ea16
Source dataset
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05962458

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes