2-Methylpiperazine → HCID 67925863, compound

HRID 981224Notes

Reaction equation

HRID 981224 reaction equation
Cl[C:2]1[C:3]([F:23])=[CH:4][C:5]2[C:6]([CH:22]=1)=[N:7][C:8]1[N:9]([CH:19]3[CH2:21][CH2:20]3)[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.[CH3:24][CH:25]1[CH2:30][NH:29][CH2:28][CH2:27][NH:26]1>N1C=CC=CC=1>[CH:19]1([N:9]2[C:8]3[N:7]=[C:6]4[CH:22]=[C:2]([N:29]5[CH2:28][CH2:27][NH:26][CH:25]([CH3:24])[CH2:30]5)[C:3]([F:23])=[CH:4][C:5]4=[CH:14][C:13]=3[C:12](=[O:15])[C:11]([C:16]([OH:18])=[O:17])=[CH:10]2)[CH2:21][CH2:20]1.[OH2:15].[CH:19]1([N:9]2[C:8]3[N:7]=[C:6]4[CH:22]=[C:2]([N:29]5[CH2:28][CH2:27][NH:26][CH:25]([CH3:24])[CH2:30]5)[C:3]([F:23])=[CH:4][C:5]4=[CH:14][C:13]=3[C:12](=[O:15])[C:11]([C:16]([OH:18])=[O:17])=[CH:10]2)[CH2:21][CH2:20]1.[CH:19]1([N:9]2[C:8]3[N:7]=[C:6]4[CH:22]=[C:2]([N:29]5[CH2:28][CH2:27][NH:26][CH:25]([CH3:24])[CH2:30]5)[C:3]([F:23])=[CH:4][C:5]4=[CH:14][C:13]=3[C:12](=[O:15])[C:11]([C:16]([OH:18])=[O:17])=[CH:10]2)[CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 660572-MethylpiperazineHCID 147005568-Chloro-1-cyclopropyl-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid

Product 2

HCID 147005751-Cyclopropyl-7-fluoro-8-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acidHCID 67925863HCID 67925863, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Cyclopropyl-7-fluoro-8-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid is prepared under the conditions of Reference Example 1 but starting from 1 g of 8-chloro-1-cyclopropyl-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid and 3 g of 2-methylpiperazine in 10 cm3 of pyridine. The pure product is obtained after a supplementary purification by recrystallization from 200 cm3 of dimethylformamide. 0.5 g of 1-cyclopropyl-7-fluoro-8-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid hemihydrate is obtained in the form of a yellow solid melting at 343° C.

Workup

  1. customThe pure product is obtained
  2. customafter a supplementary purification
  3. customby recrystallization from 200 cm3 of dimethylformamide

Sources & evidence

ORD record
ord-b0afe84c2b674e58b3ab954f13ab0ee3
Source dataset
uspto-grants-1991_02
Patent number
US04990515

Reaction notes

Loading…