2-Chloro-6,7-dimethoxy-4-quinazolinamine → HCID 20473858, compound

HRID 2295746Notes

Reaction equation

HRID 2295746 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.[C:17]1([C:23]2([C:29]([N:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)CC(C)C>[OH2:12].[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:34]2[CH2:35][CH2:36][N:31]([C:29]([C:23]3([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)=[O:30])[CH2:32][CH2:33]2)[N:3]=1

Participants

4

Reactant 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 20473809HCID 20473809, compound

Product 1

HCID 20473858HCID 20473858, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

To 25 ml of isopentanol were added 1.0 g of 4-amino-2-chloro-6,7-dimethoxyquinazoline and 1.37 g of 1-(1-phenylcyclohexylcarbonyl)piperazine, and the resulting mixture was heated under reflux for 4 hours. The crystals thereby 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 subjected to silica gel chromatography 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, to give 0.93 g of the desired Compound No. 63 hydrochloride hydrate in the form of pale yellow powdery crystals melting at 278°-279° C. (with decomposition).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customThe crystals thereby 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. washeluted with chloroform
  8. additionA 10% w/w solution of hydrogen chloride in ethanol was added to the eluate
  9. customthe crystals thus produced
  10. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-15c03769526e47b2bcc7817002984d27
Source dataset
uspto-grants-1984_01
Patent number
US04426382

Reaction notes

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