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 1718834Notes

Reaction equation

HRID 1718834 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-665263da40a744eaa9d4b0f72c8bc794
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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