1-Methylpiperazine → HCID 10114514, compound

HRID 897281Notes

Reaction equation

HRID 897281 reaction equation
Br[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)=[O:13])[C:9]([OH:24])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>CN(C=O)C>[Cl:23][C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([Cl:22])[CH:19]=1)[CH2:15][NH:14][C:12]([C:10]1[C:9]([OH:24])=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([N:29]2[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]2)[N:11]=1)=[O:13]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 10180885HCID 10180885, compound

Product 1

HCID 10114514HCID 10114514, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-bromo-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide from Example 50 (25 mg, 0.060 mmol), N-methyl piperazine (35.2 mg, 0.35 mmol) in DMF (0.25 ml) was heated at 135C for 48 hrs. The reaction mixture was diluted with DMF (0.25 ml) and purified by preparative HPLC. (Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min) to afford the title compound after lyophilization.

Workup

  1. custompurified by preparative HPLC
  2. wash(Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min)

Sources & evidence

ORD record
ord-4b0e930decc64e0fba0ddfbbb22841da
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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