Water → HCID 66585023, compound

HRID 589860Notes

Reaction equation

HRID 589860 reaction equation
[F:1][C:2]1[N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C:5]2=[C:4]([C:11]#[N:12])[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.[C:26]([N:30]=[C:31]=[O:32])([CH3:29])([CH3:28])[CH3:27].O>ClCCl>[C:26]([NH:30][C:31]([N:9]1[CH2:8][CH2:7][N:6]2[C:2]([F:1])=[C:3]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:4]([C:11]#[N:12])=[C:5]2[CH2:10]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 66584957HCID 66584957, compound

Product 1

HCID 66585023HCID 66585023, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution cooled to 0° C. of 0.75 g (3.1 mmol) of 6-fluoro-7-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carbonitrile in 50 ml of dichloromethane are added 1.4 ml (10 mmol) of triethylamine and then 0.37 g (3.7 mmol) of tert-butyl isocyanate (CAS1609-86-5) dropwise. After stirring for 2 hours at room temperature, the medium is poured into water, the organic phase is separated out and dried over sodium sulfate, and the solvent is evaporated off under reduced pressure to give a solid in the form of a green foam, which is purified by chromatography on a column of silica gel, eluting with a mixture of 20 to 50% ethyl acetate in cyclohexane, to give 0.36 g of N-tert-butyl-8-cyano-6-fluoro-7-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazine-2(1H)-carboxamide in the form of an orange-coloured gummy solid.

Workup

  1. customthe organic phase is separated out
  2. dry with materialdried over sodium sulfate
  3. customthe solvent is evaporated off under reduced pressure
  4. customto give a solid in the form of a green foam, which
  5. customis purified by chromatography on a column of silica gel
  6. washeluting with a mixture of 20 to 50% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-24e24b6c7f55424ebfc1931f8c77d33c
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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