Ammonium formate → HCID 58256374, compound

HRID 1805218Notes

Reaction equation

HRID 1805218 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][CH:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:22])[C:15]3[CH:20]=[CH:19][C:18](Cl)=[CH:17][CH:16]=3)=[CH:9][CH:8]=2)[N:6]=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:1][C:2]1[O:3][CH2:4][CH:5]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14](=[O:22])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][CH:12]=2)[N:6]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58256435HCID 58256435, compound

Product 1

HCID 58256374HCID 58256374, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of (RS)—N-[4-(2-amino-4,5-dihydro-oxazol-4-yl)-phenyl]-4-chloro-benzamide (50 mg) in methanol (3 ml) were added ammonium formate (100 mg) and palladium on charcoal (13 mg, 10 wt %) and the mixture was heated at 60° C. for 2 hours. The mixture was then cooled to room temperature, filtered through celite and the filtrate was concentrated in vacuo. The residue was taken up in ethyl acetate/THF (1:1) and this solution was washed sequentially with saturated aq. sodium bicarbonate solution and saturated brine. The organic phase was then separated, dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (Isolute® Flash-NH2 from Separtis; gradient: heptane/dichloromethane/methanol) to give (RS)—N-[4-(2-amino-4,5-dihydro-oxazol-4-yl)-phenyl]-benzamide (20 mg, 45%) as a white solid. MS (ISP): 282.1 ([M+H]+).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. washthis solution was washed sequentially with saturated aq. sodium bicarbonate solution and saturated brine
  5. customThe organic phase was then separated
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (Isolute® Flash-NH2 from Separtis; gradient: heptane/dichloromethane/methanol)

Sources & evidence

ORD record
ord-cf0c4fc87d514ab28c07369bbe77740b
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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