HCID 22346392, compound → HCID 20816857, compound

HRID 897326Notes

Reaction equation

HRID 897326 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19]([OH:20])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12]([N:21]3[CH2:26][CH2:25]S[CH2:23][CH2:22]3)[N:11]=2)=[O:9])=[CH:4][CH:3]=1.O[O:30][S:31]([O-:33])=O.[K+]>CO>[O:30]=[S:31]1(=[O:33])[CH2:25][CH2:26][N:21]([C:12]2[N:11]=[C:10]([C:8]([NH:7][CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:28][CH:27]=3)=[O:9])[C:19]([OH:20])=[C:18]3[C:13]=2[CH:14]=[CH:15][CH:16]=[N:17]3)[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 22346392HCID 22346392, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 20816857HCID 20816857, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(4-fluorobenzyl)-8-hydroxy-5-thiomorpholin-4-yl-1,6-naphthyridine-7-carboxamide (0.19 g, 0.49 mmol) in methanol (25 mL) was treated with an aqueous solution of Oxone (7.5 mL of a 1M solution, 0.75 mmol) and stirred at room temperature for 28 hr. The solvent was evaporated in vacuo and the residue partitioned between water and CH2Cl2. The organic extracts were 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. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between water and CH2Cl2
  3. customThe organic extracts were purified by reverse phase HPLC
  4. 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-aec0a0433a7d40ba874f3720def2480d
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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