1-Methylpiperazine → 3-Cyano-7-fluoro-1-methyl-8-(4-methyl-1-piperazinyl)-4-oxobenzo[b][1,8]naphthyridine

HRID 1756804Notes

Reaction equation

HRID 1756804 reaction equation
[C:1]([C:3]1[C:4](=[O:20])[C:5]2[CH:6]=[C:7]3[CH:17]=[C:16]([F:18])[C:15](F)=[CH:14][C:8]3=[N:9][C:10]=2[N:11]([CH3:13])[CH:12]=1)#[N:2].[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CS(C)=O>[C:1]([C:3]1[C:4](=[O:20])[C:5]2[CH:6]=[C:7]3[CH:17]=[C:16]([F:18])[C:15]([N:25]4[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]4)=[CH:14][C:8]3=[N:9][C:10]=2[N:11]([CH3:13])[CH:12]=1)#[N:2]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 189945833-Cyano-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 189945843-Cyano-7-fluoro-1-methyl-8-(4-methyl-1-piperazinyl)-4-oxobenzo[b][1,8]naphthyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of 2.1 g of 3-cyano-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine in 100 cm3 of dimethyl sulphoxide is heated to 80° C. in the presence of 2 cm3 of N-methylpiperazine. The reaction mixture is maintained at this temperature for 8 hours. The solution obtained is cooled to room temperature and stirred at this temperature for 15 hours. The precipitate formed is filtered off, washed with 3 times 20 cm3 of water and dried under vacuum (20 kPa) at 50° C. 2.6 g of 3-cyano-7-fluoro-1-methyl-8-(4-methyl-1-piperazinyl)-4-oxobenzo[b][1,8]naphthyridine are obtained in the form of a yellow precipitate, melting point 335° C.

Workup

  1. temperatureThe reaction mixture is maintained at this temperature for 8 hours
  2. customThe solution obtained
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. washwashed with 3 times 20 cm3 of water
  6. customdried under vacuum (20 kPa) at 50° C

Sources & evidence

ORD record
ord-e03e20b5ea8444378533beda78f4d252
Source dataset
uspto-grants-1995_08
Patent number
US05442070

Reaction notes

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