Tetrahydrofuran → HCID 117770314, compound

HRID 1526363Notes

Reaction equation

[Br:1][C:2]1[C:3](Cl)=[C:4]([C:18]#[N:19])[C:5](=O)[N:6]([C:8]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[C:15]#[N:16])[CH:7]=1.[OH2:21].[NH2:22][NH2:23].O1CCCC1>C(O)C>[NH2:19][C:18]1[C:4]2[C:5](=[O:21])[N:6]([C:8]3[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=3[C:15]#[N:16])[CH:7]=[C:2]([Br:1])[C:3]=2[NH:23][N:22]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 5-bromo-4-chloro-1-(2-cyano-6-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step F (4.35 g) and hydrazine monohydrate (0.658 mL) in ethanol (32 mL)/tetrahydrofuran (64 mL) was heated at 90° C. for 1 hr. To the reaction mixture was added hydrazine monohydrate (0.5 mL), and the mixture was heated at 90° C. for 30 min. The solvent was evaporated under reduced pressure, to the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.12 g).

Workup

customThe solvent was evaporated under reduced pressure, to the reaction mixture
additionwas added water
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-57fb750e447d45eba1784d115b6e9fb2
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085578B2

Reaction notes

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