Dimethylformamide → 2-(4-Ethoxycarboxypiperidino)carbonyl-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline hydrochloride

HRID 1003534Notes

Reaction equation

HRID 1003534 reaction equation
P(C#N)([O:6][CH2:7][CH3:8])(OCC)=O.C([N:13]([CH2:16][CH3:17])CC)C.[C:18]([C:21]1[N:30]=[C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]3[O:39][CH2:40][O:41][C:35]=3[CH:34]=2)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([Cl:42])[CH:27]=2)[N:22]=1)(O)=[O:19].N1CC[CH:46]([C:47]([O:49][CH2:50][CH3:51])=O)CC1.CN(C)C=[O:57]>O>[ClH:42].[CH2:47]([O:49][CH:50]1[CH2:17][CH2:16][N:13]([C:18]([C:21]2[N:30]=[C:29]([NH:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]4[O:39][CH2:40][O:41][C:35]=4[CH:34]=3)[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([Cl:42])[CH:27]=3)[N:22]=2)=[O:19])[CH:8]([C:7]([OH:6])=[O:57])[CH2:51]1)[CH3:46]

Participants

7

Reactant 5

HCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylateHCID 76257Diethyl cyanophosphonateHCID 187966952-Carboxy-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline

Product 1

HCID 187967612-(4-Ethoxycarboxypiperidino)carbonyl-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline hydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.50 ml (3.3 mmol) of diethyl cyanophosphate in 3 ml of dimethylformamide and 0.50 ml (3.6 mmol) of triethylamine were dropped, in this order, into a solution of 0.78 g (2.2 mmol) of 2-carboxy-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline and 0.50 g (3.2 mmol) of ethyl isonipecotate in 7 μl of dimethylformamide under cooling with ice and stirring. The obtained mixture was stirred under cooling with ice for 30 minutes and thereafter at room temperature for 3 hours, followed by the addition of water. The resulting mixture was extracted with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled in a vacuum to remove the solvent. The residue was recrystallized from hydrochloric acid/ethanol/ether to give 0.96 g of the title compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe obtained mixture was stirred
  3. temperatureunder cooling with ice for 30 minutes
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. distillationThe filtrate was distilled in a vacuum
  8. customto remove the solvent
  9. customThe residue was recrystallized from hydrochloric acid/ethanol/ether

Sources & evidence

ORD record
ord-725062ef285b46bbb13fcbc7153c805c
Source dataset
uspto-grants-2000_04
Patent number
US06046206

Reaction notes

Loading…