Trifluoromethanesulfonic acid → HCID 71499994, compound

HRID 2376635Notes

Reaction equation

HRID 2376635 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11](N)[CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)[CH:6]=[CH:7][CH:8]=1.[OH:20][S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22].N([O-])=O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([O:23][S:21]([C:24]([F:27])([F:26])[F:25])(=[O:22])=[O:20])[CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 23668193Sodium NitriteHCID 69207961HCID 69207961, compound

Product 1

HCID 71499994HCID 71499994, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-(3-methylsulfanyl-phenyl)-[1,7]naphthyridin-6-ylamine (2.05 g, 7.68 mmol) in DMF (30 ml) at 0° C. is added triflic acid (20 ml) slowly. Sodium nitrite (1.06 g) is then added slowly over 15 minutes and the reaction mixture allowed to warm to room temperature. After stirring for 23 hours the reaction is complete by HPLC. The mixture is then diluted with ethyl acetate and washed with water, 2 N sodium carbonate and brine. The organic layer is dried over magnesium sulfate and concentrated. The product is purified by silica gel chromatography, eluting with 30% ethyl acetate in isohexane. The product is obtained as an amorphous solid. MS (ES+) 400.9948

Workup

  1. washwashed with water, 2 N sodium carbonate and brine
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe product is purified by silica gel chromatography
  5. washeluting with 30% ethyl acetate in isohexane
  6. customThe product is obtained as an amorphous solid

Sources & evidence

ORD record
ord-c889b8f3bc954941a7420adb9a40deda
Source dataset
uspto-grants-2008_12
Patent number
US07468370B2

Reaction notes

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