Methanesulfonic Acid → HCID 21948178, compound

HRID 1839398Notes

Reaction equation

HRID 1839398 reaction equation
C([NH:4][C:5]1[N:14]=[C:13]2[C:8]([C:9](=[O:28])[CH:10]=[C:11]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:12]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:7]([CH3:29])[CH:6]=1)C=C.CS(O)(=O)=O>CCO.CCOC(C)=O.[Pd]>[NH2:4][C:5]1[N:14]=[C:13]2[C:8]([C:9](=[O:28])[CH:10]=[C:11]([NH:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:12]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:7]([CH3:29])[CH:6]=1

Participants

6

Reactant 2

HCID 6395Methanesulfonic AcidHCID 21948171HCID 21948171, compound

Product 1

HCID 21948178HCID 21948178, compoundYield 135.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Pd/C (30 mg, 1.75 mmol, 10%) was added to a 25 mL round bottom flask and was blanketed with argon. 7-(allylamino)-2-anilino-5-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one (150 mg, 0.392 mmol) was dissolved in EtOH (2 mL) and was added to the Pd/C followed by methane sulfonic acid (0.041 mL, 0.63 mmol). The reaction was heated to 80° C. for 3 d at which time it was cooled to room temperature, diluted with EtOAc and filtered through celite. The filtrate was concentrated in vacuo and the residue was purified by Biotage silica gel chromatrography eluting with 100% EtOAc to provide 7-amino-2-anilino-5-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one (182 mg, 41%) as a yellow solid: LCMS RT: 2.01 min, MH+: 343.3.

Workup

  1. temperaturewas cooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by Biotage silica gel chromatrography
  5. washeluting with 100% EtOAc

Sources & evidence

ORD record
ord-173fd3854da245b4b0ef3cbcc90bc774
Source dataset
uspto-grants-2004_01
Patent number
US06677352B1

Reaction notes

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