Trifluoroacetic acid → HCID 22346447, compound

HRID 897327Notes

Reaction equation

HRID 897327 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][C:26]1=[O:31].C(N(C(C)C)CC)(C)C.C(O)(C(F)(F)F)=O>CN1C(=O)N(C)CCC1>[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])[C:26](=[O:31])[CH2:27]3)[N:11]=2)=[O:13])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 81531Diisopropylethylamine2×HCID 43990421-Methylpiperazin-2-oneHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

Product 1

HCID 22346447HCID 22346447, compound

Reagents, catalysts & solvents 1

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

Procedure

A solution of 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide (0.20 g, 0.53 mmol), 1-methylpiperazin-2-one (0.21 g, 1.86 mmol) and diisopropylethylamine (0.19 mL, 1.06 mmol) in DMPU (2.0 mL) were heated at 135 C for 26 hr. Diisopropylethylamine (0.19 mL, 1.06 mmol) was added and the reaction heated at 135C for a further 24 hr. The reaction was cooled to room temperature, neutralized by the addition of TFA and purified by reverse phase HPLC. (Vydak C18, Gradient elution with Water:Acetonitrile 95:5 to 5:95 with 0.1% TFA at 30 mL/min over 15 mins). Lyophilization of the pure fractions afforded the title compound as an off white solid.

Workup

  1. custompurified by reverse phase HPLC
  2. wash(Vydak C18, Gradient elution with Water:Acetonitrile 95:5 to 5:95 with 0.1% TFA at 30 mL/min over 15 mins)

Sources & evidence

ORD record
ord-509928bcdf674d098348daffee0bcda2
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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