Ammonium formate → HCID 54313448, compound

HRID 582016Notes

Reaction equation

HRID 582016 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[C:3]=1[C:23]([NH2:25])=[O:24].C([O-])=O.[NH4+]>[Pd].CO>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[C:3]=1[C:23]([NH2:25])=[O:24]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 53789590HCID 53789590, compound

Product 1

HCID 54313448HCID 54313448, compoundYield 11.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (100 mg) was added to a de-gassed solution of the compound of Example 20 (120 mg, 0.36 mmol) and ammonium formate (30 mg, 4.8 mmol) in methanol. The reaction was stirred at room temperature and under nitrogen for 18 h. The reaction mixture was filtered through a pad of Celite® and ethanol removed under reduced pressure. The residue was purified by column chromatography (SiO2, ethyl acetate) to give the title compound (13 mg) as yellow crystals after trituration with diethyl ether m.p. 220-222°. δH (CDCl3) 7.45 (2H, d, J 8.0 Hz), 7.30-7.20 (3H, m), 6.90 (1H, d, J 7.9 Hz), 6.81 (1H, s), 6.62 (1H, d, J 8.0 Hz), 5.41 (2H, br s), 2.63 (2H br s) and 2.39 (3H, s). MS (ES+) 308 (MH+, 100%).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite® and ethanol
  2. customremoved under reduced pressure
  3. customThe residue was purified by column chromatography (SiO2, ethyl acetate)

Sources & evidence

ORD record
ord-1feda5f5de0f4c7c88ab292d1baa9201
Source dataset
uspto-grants-1999_07
Patent number
US05922741

Reaction notes

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