Hydrochloric Acid → 3-[2-[4-[[4-[(2Z)-2-methoxyimino-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 2048700Notes

Reaction equation

HRID 2048700 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][CH3:44].N1C=CC=CC=1.Cl>O.C(OCC)(=O)C>[CH3:44][O:43]/[N:42]=[C:3](/[C:2]([CH3:39])([CH3:1])[CH3:40])\[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

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 521874O-Methylhydroxylamine 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 1360637973-[2-[4-[[4-[(2Z)-2-methoxyimino-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 50.6%

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)methane hydrochloride (0.93 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 colorless crystals (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-b1a42f4943f240d5bdeea739a60141f5
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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