Ammonia → HCID 66584957, compound

HRID 589859Notes

Reaction equation

C(O[C:6](=O)[NH:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([C:15]#[N:16])[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:11]1[F:23])(C)(C)C.Cl.C=O.N>C(O)C>[F:23][C:11]1[N:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:14]2=[C:13]([C:15]#[N:16])[C:12]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 2.50 g (7.59 mmol) of tert-butyl{2-[2-fluoro-4-cyano-3-phenyl-1H-pyrrol-1-yl]ethyl}carbamate in 5 ml of ethanol are added slowly 25 ml (100 mmol) of aqueous 4N hydrochloric acid solution and 0.25 g (2.8 mmol) of paraformaldehyde. The mixture is heated at 90° C. for a further 2 hours. After cooling, the reaction medium is basified slowly by adding aqueous ammonia and the product is extracted with dichloromethane, the organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure. The black oil obtained is purified by chromatography on a column of silica gel, eluting with a mixture of 2 to 5% methanol in dichloromethane, to give 0.75 g of 6-fluoro-7-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carbonitrile in the form of a brown oil after drying.

Workup

temperatureAfter cooling
extractionthe product is extracted with dichloromethane
dry with materialthe organic phase is dried over sodium sulfate
customthe solvent is evaporated off under reduced pressure
customThe black oil obtained
customis purified by chromatography on a column of silica gel
washeluting with a mixture of 2 to 5% methanol in dichloromethane

Sources & evidence

ORD record: ord-eb4e279fa51c47fd85d3c0260a028243
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233965B2

Reaction notes

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