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Hydrochloric Acid → 3-[2-[4-[[4-[(2E)-2-ethoxyimino-3,3,3-trifluoropropyl]-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 519984
Notes
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Reaction equation

HRID 519984 reaction equation
[CH3:1][C:2]1[N:40]=[C:5]2[N:6]([CH2:33][C:34](=O)[C:35]([F:38])([F:37])[F:36])[C:7](=[O:32])[C:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]4[NH:30][C:29](=[O:31])[O:28][N:27]=4)=[CH:16][CH:15]=3)=[C:9]([CH2:10][CH2:11][CH3:12])[N:4]2[N:3]=1.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:34](/[C:35]([F:37])([F:36])[F:38])\[CH2:33][N:6]1[C:7](=[O:32])[C:8]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[NH:30][C:29](=[O:31])[O:28][N:27]=3)=[CH:18][CH:19]=2)=[C:9]([CH2:10][CH2:11][CH3:12])[N:4]2[N:3]=[C:2]([CH3:1])[N:40]=[C:5]12)[CH3:45]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 76850O-ethylhydroxylamine hydrochlorideHCID 1360637522-methyl-6-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-7-propyl-4-(3,3,3-trifluoro-2-oxopropyl) [1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one

Product 1

HCID 136063875
3-[2-[4-[[4-[(2E)-2-ethoxyimino-3,3,3-trifluoropropyl]-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
Yield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-methyl-6-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-7-propyl-4-(3,3,3-trifluoro-2-oxopropyl)[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one (0.14 g), 2-(aminooxy)ethane hydrochloride (0.37 g) and pyridine (5 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 (0.041 g, 28%).

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-6cf6d8c2eeac4dbbb67d23b214e728bd
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115136B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes