3-Ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine → HCID 54453647, compound

HRID 344902Notes

Reaction equation

HRID 344902 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18](F)=[CH:17][C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])[CH3:2].[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]1[CH2:36][NH:35][CH2:34][CH2:33][NH:32]1>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18]([N:35]4[CH2:34][CH2:33][NH:32][CH:31]([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=5[F:24])[CH2:36]4)=[CH:17][C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 98399873-Ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineHCID 137874472-(2-Fluorophenyl)piperazine

Product 1

HCID 54453647HCID 54453647, compound

Procedure

(RS)-3-Ethoxycarbonyl-7-fluoro-8-[3-(2-fluorophenyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 39, but starting with 3-ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (1.59 g) and (RS)-2-(2-fluorophenyl)piperazine (1.08 g). After recrystallization in dimethylformamide (60 cc) containing ethanol (50%), the expected product (1.3 g) is obtained in the form of a yellow solid, m.p. 228° C.

Workup

  1. customAfter recrystallization in dimethylformamide (60 cc)
  2. additioncontaining ethanol (50%)

Sources & evidence

ORD record
ord-c9a6dec8e0394047ad56b87b6663635f
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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