Ammonium formate → HCID 57667038, compound

HRID 600844Notes

Reaction equation

HRID 600844 reaction equation
C([N:8]([CH2:18][C@H:19]1[CH2:23][O:22][C:21]([NH2:24])=[N:20]1)[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([O:16][CH3:17])[CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[F:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][CH2:18][C@H:19]2[CH2:23][O:22][C:21]([NH2:24])=[N:20]2)=[CH:10][C:11]=1[O:16][CH3:17]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 25016018HCID 25016018, compound

Product 1

HCID 57667038HCID 57667038, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of (S)-4-{[benzyl-(4-fluoro-3-methoxy-phenyl)-amino]-methyl}-4,5-dihydro-oxazol-2-ylamine (150 mg, example 42) at r.t. in methanol (25 ml) were added ammonium formate (30 mg) and 10% palladium on activated charcoal (48 mg). The resulting suspension was stirred at 75° C. overnight and the mixture was then cooled to room temperature, filtered, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient:dichloromethane->dichloromethane/methanol 9:1) to give (S)-4-[(4-fluoro-3-methoxy-phenylamino)-methyl]-4,5-dihydro-oxazol-2-ylamine (39 mg, 36%) as a light yellow gum. MS (ISP): 240.1 ([M+H]+)

Workup

  1. temperaturethe mixture was then cooled to room temperature
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by column chromatography (SiO2; gradient:dichloromethane->dichloromethane/methanol 9:1)

Sources & evidence

ORD record
ord-5559db917047491fafd1cab107ebdac7
Source dataset
uspto-grants-2011_03
Patent number
US07902238B2

Reaction notes

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