Diisopropylethylamine → HCID 10739024, compound

HRID 380330Notes

Reaction equation

HRID 380330 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4](Cl)[N:3]=1.[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[C:47]([NH:51][C:52]([C@@H:54]1[CH2:59][NH:58][CH2:57][CH2:56][NH:55]1)=[O:53])([CH3:50])([CH3:49])[CH3:48].C(N(C(C)C)CC)(C)C>C(O)CC(C)C>[NH3:1].[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:58]2[CH2:57][CH2:56][NH:55][C@H:54]([C:52](=[O:53])[NH:51][C:47]([CH3:49])([CH3:48])[CH3:50])[CH2:59]2)[N:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 86757488HCID 86757488, compound

Product 2

HCID 222AmmoniaHCID 10739024HCID 10739024, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A mixture of 0.36 g of 4amino-2-chloro6,7-dimethoxyquinazoline, 1.08 g of (S)-N-tert-butyl-2-piperazinecarboxamide bis-(1S)-(+)-10-camphorsulfonate, prepared as described in U.S. Pat. No. 5,700,364, and 0.94 ml of diisopropylethylamine in 10 ml of isoamyl alcohol was heated at reflux for 9 h. After cooling to room temperature, the solvent was evaporated in vacuo and 50 ml of dichloromethane was added to the residue. The mixture was washed with water (3×20 ml), 5% aqueous Na2CO3 (30 ml), water (3×20 ml), dried (Na2SO4) and evaporated to dryness. The residue was purified by flash chromatography eluting with chloroform:2N methanolic ammonia 100:3 to give 0.173 g (30%) of the desired compound.

Workup

  1. customprepared
  2. temperatureat reflux for 9 h
  3. customthe solvent was evaporated in vacuo and 50 ml of dichloromethane
  4. additionwas added to the residue
  5. washThe mixture was washed with water (3×20 ml), 5% aqueous Na2CO3 (30 ml), water (3×20 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography
  9. washeluting with chloroform

Sources & evidence

ORD record
ord-34210192de64493bbc5e8023411876b3
Source dataset
uspto-grants-2001_10
Patent number
US06303606B1

Reaction notes

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