2-Chloro-6,7-dimethoxy-4-quinazolinamine → HCID 20473860, compound

HRID 2295749Notes

Reaction equation

HRID 2295749 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:16])[N:3]=1.[CH:17]1([CH:22]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:24])[CH2:21][CH2:20][CH2:19][CH2:18]1>C(O)CC(C)C>[ClH:16].[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:28]2[CH2:29][CH2:30][N:25]([C:23](=[O:24])[CH:22]([CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21]3)[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:26][CH2:27]2)[N:3]=1

Participants

4

Reactant 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 20473806HCID 20473806, compound

Product 1

HCID 20473860HCID 20473860, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

To 25 ml of isopentanol were added 1.2 g of 4-amino-2-chloro-6,7-dimethoxyquinazoline and 1.63 g of 1-(2-cyclopentyl-2-phenylacetyl)piperazine, and the resulting mixture was heated under reflux for 4 hours. The crystals thus produced were collected by filtration and neutralized by the addition of a 10% w/w aqueous solution of sodium hydroxide. The resulting mixture was extracted with chloroform and the extract was charged into a silica gel chromatography column and eluted with chloroform. A 10% w/w solution of hydrogen chloride in ethanol was added to the eluate and the crystals thus produced were collected by filtration, giving 1.15 g of the desired Compound No. 79 hydrochloride in the form of pale yellow powdery crystals melting at 222°-224° C. (with decomposition).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customThe crystals thus produced
  4. filtrationwere collected by filtration
  5. additionneutralized by the addition of a 10% w/w aqueous solution of sodium hydroxide
  6. extractionThe resulting mixture was extracted with chloroform
  7. additionthe extract was charged into a silica gel chromatography column
  8. washeluted with chloroform
  9. additionA 10% w/w solution of hydrogen chloride in ethanol was added to the eluate
  10. customthe crystals thus produced
  11. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-902891ae2b3648dca19bb44ef880db82
Source dataset
uspto-grants-1984_01
Patent number
US04426382

Reaction notes

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