Chloroform → HCID 19063122, compound

HRID 482485Notes

Reaction equation

HRID 482485 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]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[N:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:37]1([CH:43]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:44](O)=[O:45])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(Cl)(Cl)[Cl:54]>CN(C)C1C=CN=CC=1>[ClH:54].[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:16]2[CH2:21][CH2:20][N:19]([C:44](=[O:45])[CH:43]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH2:18][CH2:17]2)[N:3]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8333Diphenylacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline

Product 1

HCID 19063122HCID 19063122, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

2.9 g of 4-amino-6,7-dimethoxy-2-(1-piperazinyl)-quinazoline (prepared according to: J. Med. Chem. 20, 146-149 (1977)) are added in little portions, in about 10' and at room temperature, to a solution of 4.2 g dicyclohexylcarbodiimide 97% and 0.12 g of 4-dimethylaminopyridine in 60 ml CHCl3. The mixture is stirred for 10' at the same temperature and added with 2.55 g of 2,2-diphenylacetic acid and again stirred for 6 h. The residue obtained after evaporation of the solvent is purified by flash chromatography on SiO2 column elating with CHCl3 /MeOH 100:2. The fractions containing the pure base are pooled, the solvents evaporated, the residue is dissolved in warm EtOH 95% and the solution treated with HCl in EtOH about 4N. The salt which crystallizes by cooling the solution is collected by filtration and recrystallized from EtOH 90% to give 3.2 g (60%) of the wanted compound; m.p.: 282°-283° C.

Workup

  1. stirringagain stirred for 6 h
  2. customThe residue obtained
  3. customafter evaporation of the solvent
  4. customis purified by flash chromatography on SiO2 column
  5. additionThe fractions containing the pure base
  6. customthe solvents evaporated
  7. dissolutionthe residue is dissolved in warm EtOH 95%
  8. additionthe solution treated with HCl in EtOH about 4N
  9. customThe salt which crystallizes
  10. temperatureby cooling the solution
  11. filtrationis collected by filtration
  12. customrecrystallized from EtOH 90%

Sources & evidence

ORD record
ord-3ab2af9b98514de28c8b9ca91ce27caf
Source dataset
uspto-grants-1998_08
Patent number
US05798362

Reaction notes

Loading…