Hydrazine hydrate (1:1) → HCID 71114880, compound

HRID 1624044Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][CH2:12][C:11](=O)/[C:10]/2=[CH:15]\[N:16](C)C)[CH:5]=[CH:6][C:7]=1[F:8].O.[NH2:20]N>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:10]3[CH:15]=[N:16][NH:20][C:11]=3[CH2:12][CH2:13]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To the mixture of (+/−)-(2Z)-3-(3,4-difluorophenyl)-2-((dimethylamino)methylene)cyclopentanone (8.5 g, 34 mmol) in ethanol (200 mL), is added hydrazine hydrate (15 mL) and the mixture is heated to 80° C., overnight. The mixture is cooled to room temperature and concentrated in vacuo. The residue is purified by preparative HPLC using a CXTH instrument with a DAISO 10 μC18 250×50 mm column, a 9 mL injection, a flow rate of 70 mL/min, a wavelength of 214 nm and a mobile phase of 10-80% acetonitrile in 0.1% TFA/H2O to give the title compound as a white solid (2.1 g, 28%). ES/MS m/z 221 (M+H).

Workup

temperatureThe mixture is cooled to room temperature
concentrationconcentrated in vacuo
customThe residue is purified by preparative HPLC

Sources & evidence

ORD record: ord-a8add9d3dfe946c2b8dd409f5299b972
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778984B2

Reaction notes

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