Pyridine → HCID 22346348, compound

HRID 897318Notes

Reaction equation

C[CH2:2][S:3]([NH2:6])(=[O:5])=[O:4].Br[C:8]1[N:17]=[C:16]([C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[O:19])[C:15]([OH:29])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2.N1C=CC=C[CH:31]=1>>[F:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][NH:20][C:18]([C:16]2[C:15]([OH:29])=[C:14]3[C:9]([CH:10]=[CH:11][CH:12]=[N:13]3)=[C:8]([N:6]([CH3:31])[S:3]([CH3:2])(=[O:5])=[O:4])[N:17]=2)=[O:19])=[CH:23][CH:24]=1

Participants

Reactant 3

HCID 1049Pyridine

HCID 73702Ethanesulfonamide

HCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

Product 1

HCID 22346348HCID 22346348, compound

Procedure

To a mixture of methyl-methanesulfonamide (1.06 g, 9.65 mmol), 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide (1.21 g, 3.22 mmol), and Cu2O (0.46 g, 3.22 mmol) under an atmosphere of argon was added pyridine (25 mL) and the suspension was stirred at reflux for 16 hr. The reaction was allowed to cool to room temperature and the solvent evaporated in vacuo. The residue was treated with DMF (12 mL) and TFA (0.5 mL) and filtered to remove the solids. The filtrate was purified by reverse phase HPLC. (Waters PrePak 500 cartridge C18, Gradient elution with Water:Acetonitrile 95:5 to 5:95 with 0.1% TFA at 75 mL/min over 45 mins). Lyophilization of the pure fractions afforded the title compound as an off white solid.

Workup

temperatureat reflux for 16 hr
customthe solvent evaporated in vacuo
additionThe residue was treated with DMF (12 mL) and TFA (0.5 mL)
filtrationfiltered
customto remove the solids
customThe filtrate was purified by reverse phase HPLC
wash(Waters PrePak 500 cartridge C18, Gradient elution with Water:Acetonitrile 95:5 to 5:95 with 0.1% TFA at 75 mL/min over 45 mins)

Sources & evidence

ORD record: ord-ce88ff3dbfe54411befbc8350d945fc1
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921759B2

Reaction notes

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