Ammonia → HCID 59331753, compound

HRID 1255846Notes

Reaction equation

HRID 1255846 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]([C@@H:14]([NH:16][C:17]2[N:22]=[C:21]([C:23]([O:25]C)=O)[CH:20]=[N:19][CH:18]=2)[CH3:15])[CH:11]=[CH:12][CH:13]=1)=[O:6].[NH3:30]>O1CCOCC1.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]([C@@H:14]([NH:16][C:17]2[N:22]=[C:21]([C:23]([NH2:30])=[O:25])[CH:20]=[N:19][CH:18]=2)[CH3:15])[CH:11]=[CH:12][CH:13]=1)=[O:6]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 59331723HCID 59331723, compound

Product 1

HCID 59331753HCID 59331753, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (S)-methyl 6-(1-(3-(3-methylbenzamido)phenyl)ethylamino)pyrazine-2-carboxylate (40 mg, 0.1 mmol) and aqueous ammonia (4 mL, 28%) in dioxane (2 mL) was heated at 130° C. in a sealed tube for 18 hours. After this time the mixture was allowed to cool to room temperature and was diluted with ethyl acetate (20 mL). The two phases were separated and the aqueous phase extracted with ethyl acetate (10 mL). The combined organic solutions were washed with brine (15 mL), dried (Na2SO4) and concentrated under reduced pressure to give (S)-6-(1-(3-(3-methylbenzamido)phenyl)ethylamino)pyrazine-2-carboxamide (37 mg, 98%) as a beige solid.

Workup

  1. customThe two phases were separated
  2. extractionthe aqueous phase extracted with ethyl acetate (10 mL)
  3. washThe combined organic solutions were washed with brine (15 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c3fd07281c874c2e9bf02b28e61d7227
Source dataset
uspto-grants-2013_06
Patent number
US08461161B2

Reaction notes

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