Hydrochloric Acid → 3-[2-[4-[[4-[(2E)-2-ethoxyimino-3,3-dimethylbutyl]-2-methyl-5-oxo-7-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-one

HRID 1688935Notes

Reaction equation

HRID 1688935 reaction equation
[CH3:1][C:2]([CH3:40])([CH3:39])[C:3](=O)[CH2:4][N:5]1[C:10](=[O:11])[C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]3[NH:29][C:28](=[O:30])[O:27][N:26]=3)=[CH:15][CH:14]=2)=[C:8]([CH2:31][CH2:32][CH3:33])[N:7]2[N:34]=[C:35]([CH3:37])[N:36]=[C:6]12.Cl.[NH2:42][O:43][CH2:44][CH3:45].N1C=CC=CC=1.Cl>O.C(OCC)(=O)C>[CH2:44]([O:43]/[N:42]=[C:3](\[C:2]([CH3:39])([CH3:40])[CH3:1])/[CH2:4][N:5]1[C:10](=[O:11])[C:9]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]3[NH:29][C:28](=[O:30])[O:27][N:26]=3)=[CH:17][CH:18]=2)=[C:8]([CH2:31][CH2:32][CH3:33])[N:7]2[N:34]=[C:35]([CH3:37])[N:36]=[C:6]12)[CH3:45]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 76850O-ethylhydroxylamine hydrochlorideHCID 1360637264-(3,3-dimethyl-2-oxobutyl)-2-methyl-6-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one

Product 1

HCID 1360639043-[2-[4-[[4-[(2E)-2-ethoxyimino-3,3-dimethylbutyl]-2-methyl-5-oxo-7-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl]phenyl]phenyl]-4H-1,2,4-oxadiazol-5-oneYield 49.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-(3,3-dimethyl-2-oxobutyl)-2-methyl-6-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one (0.3 g), (aminooxy)ethane hydrochloride (1.1 g) and pyridine (10 mL) was stirred at 110° C. for 16 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was adjusted to pH 4 with 1 N hydrochloric acid. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.16 g, 49%).

Workup

  1. washThe ethyl acetate layer was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-57a092b07f794674bb158febea1f7a1b
Source dataset
uspto-grants-2012_04
Patent number
US08148383B2

Reaction notes

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