(2-Methanesulfonylphenyl)methanamine → 5-bromo-8-hydroxy-N-[2-(methylsulfonyl)benzyl]-1,6-naphthyridine-7-carboxamide

HRID 897368Notes

Reaction equation

HRID 897368 reaction equation
[Br:1][C:2]1[N:11]=[C:10]([C:12]([O:14]C)=O)[C:9]([OH:16])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][NH2:28])(=[O:20])=[O:19]>CO>[Br:1][C:2]1[N:11]=[C:10]([C:12]([NH:28][CH2:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[S:18]([CH3:17])(=[O:20])=[O:19])=[O:14])[C:9]([OH:16])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 16218335(2-Methanesulfonylphenyl)methanamineHCID 22343006Methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate

Product 1

HCID 223462965-bromo-8-hydroxy-N-[2-(methylsulfonyl)benzyl]-1,6-naphthyridine-7-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate (500 mg, 1.77 mmol, prepared as in Example 113) and 1-[2-(methylsulfonyl)phenyl]methanamine (491 mg, 2.65 mmol) were suspended in 10 mL methanol in an oven-dried Schlenck tube. The solution was purged with Argon for 1 minute and capped. The solution was heated to 80 deg C. with stirring over 4 days. Upon cooling a white solid precipitated out of the methanol. LCMS analysis indicated that the precipitate was the desired product. Filtration and subsequent washing with methanol (10 mL) afforded the desired material as a white solid.

Workup

  1. customThe solution was purged with Argon for 1 minute
  2. customcapped
  3. temperatureThe solution was heated to 80 deg C
  4. temperatureUpon cooling a white solid
  5. customprecipitated out of the methanol
  6. filtrationFiltration
  7. washsubsequent washing with methanol (10 mL)

Sources & evidence

ORD record
ord-c402c89ba1264ee68d23a7028b0deccd
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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