Hexahydro-1,4-diazepine → 3-Ethoxycarbonyl-7,9-difluoro-1-methyl-4-oxo-8-(perhydro-1,4-diazepin-1-yl)-1,4-dihydro-benzo[b][1,8]naphthyridine

HRID 1084403Notes

Reaction equation

HRID 1084403 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18](F)=[C:17]([F:23])[C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])[CH3:2].[NH:25]1[CH2:31][CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18]([N:25]4[CH2:31][CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[C:17]([F:23])[C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 194236883-Ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 200632913-Ethoxycarbonyl-7,9-difluoro-1-methyl-4-oxo-8-(perhydro-1,4-diazepin-1-yl)-1,4-dihydro-benzo[b][1,8]naphthyridineYield 80.8%

Procedure

The 3-ethoxycarbonyl-7,9-difluoro-1-methyl-4-oxo-8-(perhydro-1,4-diazepin-1-yl)-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 3, but starting from 2 g of 3-ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine and 2 g of hexahydro-1,4-diazepine. 2 g of 3-ethoxycarbonyl-7,9-difluoro-1-methyl-4-oxo-8-(perhydro-1,4-diazepin-1-yl)-1,4-dihydro-benzo[b][1,8]naphthyridine are obtained in the form of a yellow solid melting at 226° C.

Workup

  1. customThe 3-ethoxycarbonyl-7,9-difluoro-1-methyl-4-oxo-8-(perhydro-1,4-diazepin-1-yl)-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 3

Sources & evidence

ORD record
ord-8c54428e744a4d8283ac34d7db208575
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

Loading…