Ethyl Acetate → HCID 123334776, compound

HRID 2203684Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[C:8](/SC)=[CH:9]\[C:10]([CH:12]2[CH:17]3[CH:13]2[CH2:14][CH:15]([O:18][Si:19]([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16]3)=O)=[CH:4][C:3]=1[O:38][C:39]([F:42])([F:41])[F:40].O.[NH2:44][NH2:45].C(OCC)(=O)C>C(O)C>[Si:19]([O:18][CH:15]1[CH2:14][CH:13]2[CH:17]([CH:12]2[C:10]2[NH:45][N:44]=[C:8]([C:5]3[CH:4]=[C:3]([O:38][C:39]([F:41])([F:42])[F:40])[C:2]([NH2:1])=[N:7][CH:6]=3)[CH:9]=2)[CH2:16]1)([C:32]([CH3:34])([CH3:33])[CH3:35])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of (E)-3-(6-amino-5-(trifluoromethoxy)pyridin-3-yl)-1-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-3-(methylthio)prop-2-en-1-one (0.70 g, 1.1 mmol) and hydrazine hydrate (5 mL) in ethanol (5 mL) was sealed in a microwave vessel and heated at 100° C. by microwave irradiation for 1 h. The reaction mixture was concentrated, and the resulting residue was purified by flash column chromatography (60% ethyl acetate in petroleum ether) to product as a white solid (0.50 g, 76% yield). LCMS (ESI) [MH]+=579.1.

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-1f646e8619ca459ba262a5cfebc079fb
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365583B2

Reaction notes

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