Hydroxyamine hydrochloride → HCID 66690716, compound

HRID 1846394Notes

Reaction equation

C([O-])(=O)C.[Na+].[CH:6]1([C:9](=O)[C:10](=[CH:32]OCC)[C:11]([C:13]2[C:18](=[O:19])[N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:15][CH:14]=2)=[O:12])[CH2:8][CH2:7]1.Cl.[NH2:38][OH:39]>C(O)C.C(OCC)(=O)C>[CH:6]1([C:9]2[O:39][N:38]=[CH:32][C:10]=2[C:11]([C:13]2[C:18](=[O:19])[N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:15][CH:14]=2)=[O:12])[CH2:8][CH2:7]1

Participants

Conditions

Temperature: 0 °C

Procedure

Anhydrous sodium acetate (68 mg, 0.83 mmol) was added to a solution of 1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-2-(ethoxymethylene)-1,3-propanedione (i.e. the product from Example 6, Step B) (171 mg, 0.41 mmol) in ethanol (4 mL) at 0° C. Hydroxylamine hydrochloride (29 mg, 0.42 mmol) was added and the resulting suspension was stirred at 0° C. for 30 min and then at ambient temperature for 2 h. The resulting mixture was diluted with ethyl acetate (20 mL) and ethanol (20 mL), concentrated onto 0.8 g silica gel, and the residue purified by medium pressure liquid chromatography using a 12 g silica gel column and eluting with 0 to 100% ethyl acetate in hexanes to obtain 14 mg of the title compound, a compound of the present invention as a yellow glassy solid.

Workup

waitat ambient temperature for 2 h
concentrationconcentrated onto 0.8 g silica gel
customthe residue purified by medium pressure liquid chromatography
washeluting with 0 to 100% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-32e6762a92a040f9ad012f890df4d112
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952024B2

Reaction notes

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