2-Chloro-6,7-dimethoxy-4-quinazolinamine → HCID 13723660, compound

HRID 1448962Notes

Reaction equation

HRID 1448962 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.[O:17]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[O:20][CH2:19][CH:18]1[C:27]([N:29]1[CH2:35][CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28]>C(O)CCC>[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:32]2[CH2:33][CH2:34][CH2:35][N:29]([C:27]([CH:18]3[O:17][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[O:20][CH2:19]3)=[O:28])[CH2:30][CH2:31]2)[N:3]=1

Participants

4

Reactant 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 13723686(2,3-Dihydro-1,4-benzodioxin-2-yl)(hexahydro-1H-1,4-diazepin-1-yl)methanone

Product 1

HCID 13723660HCID 13723660, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4-Amino-2-chloro-6,7-dimethoxyquinazoline (1.58 g.) and N-(1,4-benzodioxan-2-carbonyl)homopiperazine (2.0 g.) were heated under reflux in n-butanol (114 ml.) for 60 hours. The mixture was then cooled, butanol removed in vacuo and the solid residue triturated with ether, taken up in hot methanol, filtered and cooled. The solid product was collected, then the residual solution was evaporated in vacuo and the residue taken up in hot isopropanol, cooled, filtered, then re-evaporated in vacuo. The residue was combined with the original solid product, treated with cold methanol, and recrystallized from ethanol to give 4-amino-2-[4-(1,4-benzodioxan-2-carbonyl)homopiperazin-1-yl]-6,7-dimethoxyquinazoline hydrochloride (0.57 g.), m.p. 250°-251° C.

Workup

  1. temperatureThe mixture was then cooled
  2. custombutanol removed in vacuo
  3. customthe solid residue triturated with ether
  4. filtrationfiltered
  5. temperaturecooled
  6. customThe solid product was collected
  7. customthe residual solution was evaporated in vacuo
  8. temperaturecooled
  9. filtrationfiltered
  10. customre-evaporated in vacuo
  11. additiontreated with cold methanol
  12. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7e753f9957b1465d8a0e64281c8e7269
Source dataset
uspto-grants-1980_02
Patent number
US04188390

Reaction notes

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