Ammonia → HCID 59331753, compound

HRID 572220Notes

Reaction equation

HRID 572220 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-8a4f262ed9124feb9ecfb20937e295b4
Source dataset
uspto-grants-2015_05
Patent number
US09029386B2

Reaction notes

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