Triethylamine → HCID 54761630, compound

HRID 589888Notes

Reaction equation

HRID 589888 reaction equation
[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C:5]2=[C:4]([C:11]([NH2:13])=[O:12])[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1.C(N(CC)CC)C.[C:28]([N:32]=[C:33]=[O:34])([CH3:31])([CH3:30])[CH3:29].[OH-].[Na+]>>[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:33]([NH:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:34])[CH2:10][C:5]2=[C:4]([C:11]([NH2:13])=[O:12])[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 62412tert-Butyl isocyanateHCID 66585015HCID 66585015, compound

Product 1

HCID 54761630HCID 54761630, compoundYield 51.5%

Procedure

To a suspension of 0.24 g (0.71 mmol) of 6-bromo-7-(3-fluorophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxamide is added 0.30 ml (2.13 mmol) of triethylamine and then, at 0° C., 0.10 ml (0.85 mmol) of tert-butyl isocyanate. After reaction for 1 hour at room temperature, the mixture is treated with aqueous 1N sodium hydroxide solution and the product is extracted with dichloromethane. The organic phase is dried over sodium sulfate and filtered, and the solvent is evaporated off under reduced pressure. The residue is purified by chromatography on a column of 40 g of silica gel, eluting with a mixture of 4% methanol in dichloromethane, to give 0.16 g of 6-bromo-7-(3-fluorophenyl)-N2-(tert-butyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide in the form of a powder after recrystallization from 10 ml of acetonitrile, filtering and drying under reduced pressure.

Workup

  1. customat 0° C.
  2. customAfter reaction for 1 hour at room temperature
  3. extractionthe product is extracted with dichloromethane
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent is evaporated off under reduced pressure
  7. customThe residue is purified by chromatography on a column of 40 g of silica gel
  8. washeluting with a mixture of 4% methanol in dichloromethane

Sources & evidence

ORD record
ord-c758c3348209443093dac5c0ea65c719
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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