Hydrochloric Acid → HCID 136052405, compound

HRID 1889585Notes

Reaction equation

[CH2:1]([C:3]1[S:41][C:6]2[N:7]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[C:35]4[NH:39][C:38](=[O:40])[O:37][N:36]=4)=[CH:25][CH:24]=3)[C:8](=[O:21])[N:9]([CH2:12][C:13](=O)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10](=O)[C:5]=2[CH:4]=1)[CH3:2].Cl.[NH2:43][O:44][CH2:45]C=C.N1C=CC=CC=1.Cl.[OH2:55]>C(Cl)(Cl)Cl.C(O)C>[CH2:1]([C:3]1[S:41][C:6]2[N:7]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[C:35]4[NH:39][C:38](=[O:40])[O:37][N:36]=4)=[CH:27][CH:28]=3)[C:8](=[O:21])[N:9]([CH2:12][C:13](=[N:43][O:44][CH3:45])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:10](=[O:55])[C:5]=2[CH:4]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-ethyl-1-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-3-(2-oxo-2-phenylethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.3 g), 3-(aminooxy)prop-1-ene hydrochloride (0.05 g), pyridine (10 mL) and ethanol (10 mL) was stirred at 100° C. for 16 hr. To the reaction mixture were added chloroform and water, and the mixture was adjusted to pH 4 with 1N hydrochloric acid. The chloroform 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 stereoisomer mixture (0.22 g, 74%).

Workup

washThe chloroform 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-c8e650506770419798aac7161eedca30
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501750B2

Reaction notes

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