Pyridine → 3-[2-[4-[[4-butyl-1-[(2Z)-3,3-dimethyl-2-propan-2-yloxyiminobutyl]-2-methyl-6-oxopyrimidin-5-yl]methyl]-3-fluorophenyl]phenyl]-4H-1,2,4-oxadiazol-5-one

HRID 1674164Notes

Reaction equation

HRID 1674164 reaction equation
[CH2:1]([C:5]1[N:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13](=O)[C:14]([CH3:17])([CH3:16])[CH3:15])[C:7](=[O:19])[C:6]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[NH:37][C:36](=[O:38])[O:35][N:34]=2)=[CH:23][C:22]=1[F:39])[CH2:2][CH2:3][CH3:4].Cl.[NH2:41][O:42][CH:43]([CH3:45])[CH3:44].N1C=CC=CC=1>C(OCC)(=O)C>[CH2:1]([C:5]1[N:10]=[C:9]([CH3:11])[N:8]([CH2:12]/[C:13](=[N:41]\[O:42][CH:43]([CH3:45])[CH3:44])/[C:14]([CH3:15])([CH3:16])[CH3:17])[C:7](=[O:19])[C:6]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[NH:37][C:36](=[O:38])[O:35][N:34]=2)=[CH:23][C:22]=1[F:39])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12696235O-(propan-2-yl)hydroxylamine hydrochlorideHCID 1360269906-butyl-3-(3,3-dimethyl-2-oxobutyl)-5-{[3-fluoro-2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-2-methylpyrimidin-4(3H)-one

Product 1

HCID 1361469013-[2-[4-[[4-butyl-1-[(2Z)-3,3-dimethyl-2-propan-2-yloxyiminobutyl]-2-methyl-6-oxopyrimidin-5-yl]methyl]-3-fluorophenyl]phenyl]-4H-1,2,4-oxadiazol-5-oneYield 22%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-butyl-3-(3,3-dimethyl-2-oxobutyl)-5-{[3-fluoro-2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-2-methylpyrimidin-4(3H)-one (0.15 g), 2-(aminooxy)propane hydrochloride (0.63 g) and pyridine (5 mL) was stirred at 100° C. for 16 hr. The mixture was allowed to cool to room temperature, and the reaction mixture was diluted with ethyl acetate, washed with 1 M hydrochloric acid and then with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.036 g, 22%).

Workup

  1. temperatureto cool to room temperature
  2. washwashed with 1 M hydrochloric acid
  3. dry with materialwith saturated brine, and dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8bc0222e94ba4a469ae44ae64b7e8eb7
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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