Piperazine → 1-Cyclopropyl-3-ethoxycarbonyl-7,9-difluoro-4-oxo-8-(1-piperazinyl)-1,4-dihydro-benzo[b][1,8]naphthyridine

HRID 1084413Notes

Reaction equation

HRID 1084413 reaction equation
[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[C:14]([F:20])=[C:15](F)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.[NH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>>[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[C:14]([F:20])=[C:15]([N:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 185491641-Cyclopropyl-3-ethoxycarbonyl-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 200632981-Cyclopropyl-3-ethoxycarbonyl-7,9-difluoro-4-oxo-8-(1-piperazinyl)-1,4-dihydro-benzo[b][1,8]naphthyridineYield 56.4%

Procedure

The 1-cyclopropyl-3-ethoxycarbonyl-7,9-difluoro-4-oxo-8-(1-piperazinyl)-1,4-dihydro-benzo[b][1,8]naphthyridine was prepared under the conditions of Example 35 but starting from 1.5 g of 1-cyclopropyl-3-ethoxycarbonyl-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine and 2.7 g of piperazine. After recrystallizing once from 40 cm3 of propan-2-ol, 1 g of 1-cyclopropyl-3-ethoxycarbonyl-7,9-difluoro-4-oxo-8-(1-piperazinyl)-1,4-dihydro-benzo[b][1,8]naphthyridine is obtained in the form of a yellow solid melting at 256° C.

Workup

  1. customThe 1-cyclopropyl-3-ethoxycarbonyl-7,9-difluoro-4-oxo-8-(1-piperazinyl)-1,4-dihydro-benzo[b][1,8]naphthyridine was prepared under the conditions of Example 35
  2. customAfter recrystallizing once from 40 cm3 of propan-2-ol

Sources & evidence

ORD record
ord-b2a66c68f8c14de99f63948bb97e1465
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

Loading…