Ammonia → HCID 66584957, compound

HRID 1630004Notes

Reaction equation

HRID 1630004 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

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 66585013HCID 66585013, compound

Product 1

HCID 66584957HCID 66584957, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

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

Sources & evidence

ORD record
ord-4832f1d86b5e434bbc6504201ff6820f
Source dataset
uspto-grants-2014_07
Patent number
US08791119B2

Reaction notes

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