2-Chloro-6,7-dimethoxy-4-quinazolinamine → 8-[1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-3-piperidinyl]-8-azaspiro[4,5]decan-7,9-dione hydrochloride
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([N:7]2[C:16](=[O:17])[CH2:15][C:10]3([CH2:14][CH2:13][CH2:12][CH2:11]3)[CH2:9][C:8]2=[O:18])[CH2:2]1.[NH2:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[C:22]([Cl:34])[N:21]=1>C(O)CC(C)C>[ClH:34].[NH2:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[C:22]([N:1]2[CH2:6][CH2:5][CH2:4][CH:3]([N:7]3[C:8](=[O:18])[CH2:9][C:10]4([CH2:14][CH2:13][CH2:12][CH2:11]4)[CH2:15][C:16]3=[O:17])[CH2:2]2)[N:21]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The mixture of 3.75 g of 8-(3-piperidinyl)-8-azaspiro [4,5]decan-7,9 -dione, 3.59 g of 4-amino-2-chloro-6,7-dimethoxyquinazoline and 100 ml of isoamyl alcohol is stirred and refluxed under nitrogen for 24 hours. It is cooled to 20°, the solids filtered off, washed with isoamyl alcohol and diethyl ether and recrystallized from the mixture of 160 ml of methanol and 110 ml of water, to yield the 8-[1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-3-piperidinyl]-8-azaspiro[4,5]decan-7,9-dione hydrochloride melting at 311°-312° with decomposition.
Workup
- temperaturerefluxed under nitrogen for 24 hours
- temperatureIt is cooled to 20°
- filtrationthe solids filtered off
- washwashed with isoamyl alcohol and diethyl ether
- customrecrystallized from the mixture of 160 ml of methanol and 110 ml of water
Sources & evidence
- ORD record
- ord-79759314c32d460ea16ec8d0fa971d1c
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04255429
Reaction notes
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