Trifluoroacetic acid → HCID 20816856, compound

HRID 897317Notes

Reaction equation

HRID 897317 reaction equation
[CH2:1]1[CH2:7][S:4](=[O:6])(=[O:5])[NH:3][CH2:2]1.Br[C:9]1[N:18]=[C:17]([C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[O:20])[C:16]([OH:30])=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2.C(=O)([O-])[O-].[K+].[K+].C(O)(C(F)(F)F)=O>[Cu].CN(C=O)C>[O:5]=[S:4]1(=[O:6])[CH2:7][CH2:1][CH2:2][N:3]1[C:9]1[N:18]=[C:17]([C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[O:20])[C:16]([OH:30])=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 6421571,3-PropanesultamHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

Product 1

HCID 20816856HCID 20816856, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,3 propanesultam (prepared as in White et al, J. Org Chem. 1987, 52: 2162) (0.081 g, 0.66 mmol), 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide (0.10 g, 0.27 mmol), potassium carbonate (0.092 g, 0.66 mmol) and copper powder (0.017 g, 0.27 mmol) under an atmosphere of argon was stirred at 160C for 16 hr. The reaction was allowed to cool to room temperature and the residue was treated with DMF (5 mL) and TFA (1.5 mL) and filtered through a pad of celite 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

  1. filtrationfiltered through a pad of celite
  2. customto remove the solids
  3. customThe filtrate was purified by reverse phase HPLC
  4. 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-82f62c54d58843a0a54b4abb7ae6b40d
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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