Hydrochloric Acid → HCID 21717267, compound

HRID 1386261Notes

Reaction equation

HRID 1386261 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8](C(OCC)OCC)[C:7](=[O:19])[CH:6]2[C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:32][CH2:33][CH2:34][O:35][CH3:36])=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][N:21]=1>C(O)C>[Br:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:19])[CH:6]2[C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:32][CH2:33][CH2:34][O:35][CH3:36])=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][N:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21717217HCID 21717217, compound

Product 1

HCID 21717267HCID 21717267, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2M Hydrochloric acid (2.75 ml, 5.5 mmol) was added to a solution of 4-(5-bromo-1-diethoxymethyloxindol-3-yl)-6-methoxy-7-(2-methoxyethoxy)quinazoline (300 mg, 0.55 mmol) in ethanol (20 ml) at 90° C. The mixture was heated for 1 hour, the solid product was collected by filtration and purified on a Diaion (trade mark of Mitsubishi) HP20SS resin column, eluting with acetonitrile (using a gradient of 0 to 100%) in hydrochloric acid (pH2). Concentration of the fractions by evaporation gave a precipitate which was collected by filtration, washed with water to give a solid which was purified again by column flash chromatography using an increasingly polar mixture of methylene chloride/methanol (95/5 to 80/20) as eluent. After evaporation of the solvent, the resulting solid was dissolved in a minimum volume of methanol and a 2.9M solution of hydrogen chloride in ether was added to the solution. The solid was collected by filtration, washed with ether and dried under vacuum to give 4-(5-bromooxindol-3-yl)-6-methoxy-7-(2-methoxyethoxy)quinazoline as a hydrochloride salt (74 mg, 30%) as an orange solid.

Workup

  1. temperatureThe mixture was heated for 1 hour
  2. filtrationthe solid product was collected by filtration
  3. custompurified on a Diaion (trade mark of Mitsubishi) HP20SS resin column
  4. washeluting with acetonitrile (
  5. customConcentration of the fractions by evaporation
  6. customgave a precipitate which
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customto give a solid which
  10. customwas purified again by column flash chromatography
  11. additionan increasingly polar mixture of methylene chloride/methanol (95/5 to 80/20) as eluent
  12. customAfter evaporation of the solvent
  13. dissolutionthe resulting solid was dissolved in a minimum volume of methanol
  14. additiona 2.9M solution of hydrogen chloride in ether was added to the solution
  15. filtrationThe solid was collected by filtration
  16. washwashed with ether
  17. customdried under vacuum

Sources & evidence

ORD record
ord-5a7c2c4efc174997bbb671af5889c37a
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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