Hydrochloric Acid → HCID 178438489, compound

HRID 2062995Notes

Reaction equation

[O:1]=[C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]3[C:21](=[O:43])[N:22]([C@H:32]4[CH2:37][CH2:36][C@H:35]([O:38][CH2:39][C:40](=O)[CH3:41])[CH2:34][CH2:33]4)[C:23]4[N:24]([N:29]=[CH:30][N:31]=4)[C:25]=3[CH2:26][CH2:27][CH3:28])=[CH:15][CH:14]=2)[NH:3]1.Cl.[NH2:45][O:46][CH3:47].N1C=CC=CC=1.Cl>O.C(OCC)(=O)C>[CH3:47][O:46]/[N:45]=[C:40](\[CH3:41])/[CH2:39][O:38][C@H:35]1[CH2:34][CH2:33][C@H:32]([N:22]2[C:21](=[O:43])[C:20]([CH2:19][C:16]3[CH:17]=[CH:18][C:13]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[C:4]4[NH:3][C:2](=[O:1])[O:6][N:5]=4)=[CH:14][CH:15]=3)=[C:25]([CH2:26][CH2:27][CH3:28])[N:24]3[N:29]=[CH:30][N:31]=[C:23]23)[CH2:37][CH2:36]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-4-[trans-4-(2-oxopropoxy)cyclohexyl]-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one (0.095 g), (aminooxy)methane hydrochloride (0.041 g) and pyridine (5 mL) was stirred at 80° 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 (0.07 g, 70%).

Workup

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

Sources & evidence

ORD record: ord-d872ac0a0b03456b815c407e4bcb7a97
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283353B2

Reaction notes

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