Hexahydro-1,4-diazepine → (1,4-Diazepan-1-yl)(oxolan-2-yl)methanone

HRID 442103Notes

Reaction equation

HRID 442103 reaction equation
N1CCCNCC1.O1C=CC=C1C(Cl)=O.[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21]([N:23]1[CH2:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22]>>[O:16]1[CH2:20][CH2:19][CH2:18][CH:17]1[C:21]([N:23]1[CH2:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22]

Participants

4

Reactant 3

HCID 68163Hexahydro-1,4-diazepineHCID 682422-Furancarbonyl chlorideHCID 12694336(1,4-diazepan-1-yl)(furan-2-yl)methanone

Product 1

HCID 13100546(1,4-Diazepan-1-yl)(oxolan-2-yl)methanone

Procedure

In the illustrated reactions, the compound of Formula II is prepared by reacting hexahydro-1,4-diazepine with furoyl chloride in an acid solution. The resultant 1-(2-furoyl)-hexahydro-1,4-diazepine is hydrogenated to produce 1-(tetrahydro-2-furoyl)-hexahydro-1,4-diazepine which is reacted with 2-chloro-4-amino-6,7-dimethoxyquinazoline in the presence of methoxy ethanol to give the compound 2-[4-(tetrahydro-2-furoyl)-hexahydro-1,4-diazepinyl-1]-4-amino-6,7-dimethoxy quinazoline. The hydrochloride salt is prepared by acidifying with hydrogen chloride.

Sources & evidence

ORD record
ord-75f1392c8845479589bb0ae4645487e0
Source dataset
uspto-grants-1977_08
Patent number
US04044135

Reaction notes

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