Isopropanol → 2-[N-(3-Ethoxycarbonylpropyl)-N-methylamino]-4-(3,4-methylenedioxybenzyl)amino-6-cyanoquinazoline

HRID 2392896Notes

Reaction equation

HRID 2392896 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].C(N(CC)CC)C.CC(O)C.Cl[C:24]1[N:33]=[C:32]([NH:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]3[O:42][CH2:43][O:44][C:38]=3[CH:37]=2)[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:45]#[N:46])[CH:30]=2)[N:25]=1>CN(C)C=O>[CH2:10]([O:9][C:7]([CH2:6][CH2:5][CH2:4][N:3]([C:24]1[N:33]=[C:32]([NH:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]3[O:42][CH2:43][O:44][C:38]=3[CH:37]=2)[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:45]#[N:46])[CH:30]=2)[N:25]=1)[CH3:2])=[O:8])[CH3:11]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8471TriethylamineHCID 14177893Ethyl 4-(methylamino)butanoate hydrochlorideHCID 211839842-Chloro-4-(3,4-methylenedioxybenzyl)amino-6-cyanoquinazoline

Product 1

HCID 220693432-[N-(3-Ethoxycarbonylpropyl)-N-methylamino]-4-(3,4-methylenedioxybenzyl)amino-6-cyanoquinazolineYield 77.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

858 mg of ethyl N-methyl-4-aminobutyrate hydrochloride, 238 mg of triethylamine, 4 ml of 2-propanol and 2 ml of N,N-dimethylformamide were added to 400 mg of 2-chloro-4-(3,4-methylenedioxybenzyl)amino-6-cyanoquinazoline. The obtained mixture was refluxed for 1 hour, cooled to room temperature and filtered. The filtrate was distilled under a reduced pressure to remove the solvent and the residue was recrystallized (from ethanol/water) to give 410 mg of the title compound.

Workup

  1. temperatureThe obtained mixture was refluxed for 1 hour
  2. filtrationfiltered
  3. distillationThe filtrate was distilled under a reduced pressure
  4. customto remove the solvent
  5. customthe residue was recrystallized (from ethanol/water)

Sources & evidence

ORD record
ord-c9a15561ff6c43e1930b149bf7e864fc
Source dataset
uspto-grants-1998_09
Patent number
US05801180

Reaction notes

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