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

HRID 1420952Notes

Reaction equation

HRID 1420952 reaction equation
[F:1][C:2]1[CH:29]=[C:28]([CH3:30])[C:27]([O:31]C(OC)=O)=[CH:26][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][N:6]=1.[OH-].[Na+].O.[ClH:39]>CO>[ClH:39].[F:1][C:2]1[CH:29]=[C:28]([CH3:30])[C:27]([OH:31])=[CH:26][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=3)=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 226250584-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)-6-methoxy-7-(2-(4-pyridyl)ethoxy)quinazoline

Product 1

HCID 226249174-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(2-(4-pyridyl)ethoxy)quinazoline hydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 4-(2-fluoro-5-methoxycarbonyloxy4-methylanilino)-6-methoxy-7-(2-(4-pyridyl)ethoxy)quinazoline (300 mg, 0.63 mmol) and 2M aqueous sodium hydroxide (0.38 ml, 0.76 mmol) in methanol (6 ml) was stirred at ambient temperature for 2 hours. Water was added and the mixture adjusted to pH7 with 2M hydrochloric acid. The precipitate was collected by filtration, washed with water, and dried under vacuum. The solid was dissolved in methylene chloride/methanol and a 5M solution of hydrogen chloride in isopropanol (0.5 ml) was added. The mixture was diluted with isopropanol, and the methylene chloride and methanol solvents were removed by evaporation. The resulting precipitate was collected by filtration, washed with methylene chloride and dried under vacuum to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(2-(4-pyridyl)ethoxy)quinazoline hydrochloride (270 mg, 94%).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried under vacuum
  4. dissolutionThe solid was dissolved in methylene chloride/methanol
  5. additiona 5M solution of hydrogen chloride in isopropanol (0.5 ml) was added
  6. additionThe mixture was diluted with isopropanol
  7. customthe methylene chloride and methanol solvents were removed by evaporation
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with methylene chloride
  10. customdried under vacuum

Sources & evidence

ORD record
ord-70c08797268b4c9e8285e256ac1ebd4c
Source dataset
uspto-grants-2000_06
Patent number
US06071921

Reaction notes

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