Trifluoroacetic acid → HCID 15958274, compound

HRID 897298Notes

Reaction equation

HRID 897298 reaction equation
Br[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:13])[C:9]([OH:23])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.[C:31]([OH:37])([C:33]([F:36])([F:35])[F:34])=[O:32]>CN1C(=O)N(C)CCC1>[F:34][C:33]([F:36])([F:35])[C:31]([O-:37])=[O:32].[NH:11]1[CH2:10][CH2:12][NH2+:14][CH2:15][CH2:16]1.[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][NH:14][C:12]([C:10]2[C:9]([OH:23])=[C:8]3[C:3]([CH:4]=[CH:5][CH:6]=[N:7]3)=[C:2]([N:28]3[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]3)[N:11]=2)=[O:13])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 531671-MethylpiperazineHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

Product 2

HCID 15958274HCID 15958274, compoundHCID 21903395HCID 21903395, compound

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

To a solution of 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide from example 126 (45 mg, 0.120 mmol), N-methylpiperazine (79.8 ul, 0.72 mmol) in DMPU (0.50 ml) was heated at 135 C for 18 hrs. The resulting mixture was treated with TFA (100 ul) 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%) at 15 ml/min) to afford the piperazin-4-ium trifluoroacetate salt of the title compound after lyophillization.

Workup

  1. custompurified by preparative HPLC (Gilson Semi Preparative HPLC System
  2. washa YMC Combiprep Pro Column (50×20 mm i.d., C18, S-5 um, 120A) eluting with 5-95% acetonitrile/water (0.1%) at 15 ml/min)

Sources & evidence

ORD record
ord-149f74489de94eba80d117f61ea8be27
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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