p-Toluenesulfonic acid monohydrate → HCID 59815654, compound

HRID 499054Notes

Reaction equation

HRID 499054 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20]CC3C=CC=CC=3)=[CH:16][CH:15]=2)=[N:6][CH:5]=1.O.[C:30]1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(OCC)(=O)C.C(OC)(OC)OC.[Pd]>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]2[N:10]=[CH:30][N:13]([C:14]3[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=3)[C:7]2=[N:6][CH:5]=1)=[O:28]

Participants

7

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 598156466-(4-Benzyloxyphenylamino)-5-nitronicotinic acid methyl ester

Product 1

HCID 59815654HCID 59815654, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 9005Trimethyl orthoformateSolvent

Procedure

To a suspension of XXIV (235 mg, 0.62 mmol) in MeOH (3 mL) and ethyl acetate (3 mL) was added 10% Pd—C (47 mg) under nitrogen atmosphere. The resulting mixture was hydrogenated at rt overnight. The catalyst was removed by filtration under nitrogen and washed with methanol, the filtrate was concentrated under reduced pressure to give a white solid. MS (ES, Pos.): m/z 260 [MH+]. The hydrogenation product was suspended in trimethyl orthoformate (5 mL), and p-toluenesulfonic acid monohydrate (12 mg, 0.062 mmol) was added. The resulting mixture was stirred at rt overnight. The white solid was collected by filtration. MS (ES, Pos.): m/z 270 [MH+]. 1H NMR (CD3OD, 400 MHz): δ=3.99 (s, 3H), 7.00 (d, J=8.8 Hz, 2H), 7.59 (d, J=8.8 Hz, 2H), 8.71 (d, J=1.8 Hz, 1H), 8.72 (s, 1H), 9.05 (d, J=1.8 Hz, 1H).

Workup

  1. customThe catalyst was removed by filtration under nitrogen
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give a white solid
  5. filtrationThe white solid was collected by filtration

Sources & evidence

ORD record
ord-70af0a7279054914964cfe8bacdbc353
Source dataset
uspto-grants-2010_08
Patent number
US07767673B2

Reaction notes

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