Ethanol → HCID 57749251, compound

HRID 1874457Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:28]=[CH:29][C:30]=1[CH3:31])[O:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20]([NH:22]C(=O)OCC)=S)=[N:17][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].O[NH3+].C([N:38](CC)C(C)C)(C)C.C(O)C>CO>[NH2:38][C:20]1[N:19]=[C:16]2[CH:15]=[CH:14][C:13]([O:12][C:11]3[CH:28]=[CH:29][C:30]([CH3:31])=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH:10]=3)=[CH:18][N:17]2[N:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of ethyl {[(5-{3-[(tert-butoxycarbonyl)amino]-4-methylphenoxy}pyridin-2-yl)amino]carbonothioyl}carbamate (11.5 g, 15.4 mmol), hydroxylammonium chloride (15.4 g, 0.223 mol), N,N-diisopropylethylamine (23.0 mL, 0.132 mol), ethanol (200 mL) and methanol (200 mL) was stirred at 80° C. for 12 hr. The reaction solution was concentrated under reduced pressure and ethyl acetate was added to the residue. The mixture was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate-hexane to give the title compound (9.18 g, 100%) as a white solid.

Workup

concentrationThe reaction solution was concentrated under reduced pressure and ethyl acetate
additionwas added to the residue
washThe mixture was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltrated
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-6cb6db0feb914e08acc3db5d93d14b85
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304557B2

Reaction notes

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