Hydroxyamine hydrochloride → HCID 16047910, compound

HRID 905520Notes

Reaction equation

Cl.[NH2:2][OH:3].[Cl:4][C:5]1[C:6]([N:11]2[C:15]([C:16]([NH:18][C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[C:27](=O)[C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29])=[O:17])=[CH:14][C:13]([C:36]([F:39])([F:38])[F:37])=[N:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1.C([O-])(=O)C.[Na+]>O.C(O)C>[Cl:4][C:5]1[C:6]([N:11]2[C:15]([C:16]([NH:18][C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3/[C:27](=[N:2]/[OH:3])/[C:28]([N:30]([CH2:31][CH3:32])[CH2:33][CH3:34])=[O:29])=[O:17])=[CH:14][C:13]([C:36]([F:38])([F:37])[F:39])=[N:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of hydroxylamine hydrochloride (50 mg, 0.71 mmol) in water (0.5 mL) was added to a solution of 1-(3-chloro-2-pyridinyl)-N-[2-[(diethylamino)oxoacetyl]-4,6-dimethylphenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide (i.e. the title product of Example 2, 124 mg, 0.24 mmol) in ethanol (5 mL) at 25° C. The resulting mixture was treated with a solution of sodium acetate (200 mg) in water (2 mL). The resulting mixture was heated at reflux for 3 days and then cooled to 25° C., diluted with ethanol (30 mL) and concentrated onto silica gel (0.5 g). The residue was purified by flash chromatography on silica gel eluted with 35% ethyl acetate in hexanes to give 50 mg of the title product, a compound of the present invention, as a yellow glassy solid.

Workup

temperatureThe resulting mixture was heated
temperatureat reflux for 3 days
concentrationconcentrated onto silica gel (0.5 g)
customThe residue was purified by flash chromatography on silica gel
washeluted with 35% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-316ef3f7b4ed48edac9e493bced5fc41
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012499B2

Reaction notes

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