Acetic Acid → 5-((1R,2S)-2-aminocyclohexylamino)-3-(4-carbamoylphenylamino)pyrazine-2-carboxamide

HRID 332750Notes

Reaction equation

HRID 332750 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[N:10]=[C:11]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)[C:12]([C:15]#[N:16])=[N:13][CH:14]=1.[OH-:26].[Na+].[OH:28]O.CC(O)=O>CCO.CS(C)=O>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[N:10]=[C:11]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([C:24](=[O:28])[NH2:25])=[CH:22][CH:23]=2)[C:12]([C:15]([NH2:16])=[O:26])=[N:13][CH:14]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 866855545-((1R,2S)-2-aminocyclohexylamino)-3-(4-cyanophenylamino)pyrazine-2-carbonitrile

Product 1

HCID 866855555-((1R,2S)-2-aminocyclohexylamino)-3-(4-carbamoylphenylamino)pyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

The compound 5-((1R,2S)-2-aminocyclohexylamino)-3-(4-cyanophenylamino)pyrazine-2-carbonitrile (40 mg) was dissolved in EtOH (2 mL) and DMSO (1 mL), aq. 1N NaOH (1.0 mL) and aq. H2O2 (50%, 1.0 mL) were added. The mixture was stirred at room temperature for 30 min. HOAc (0.5 mL) was added. The mixture was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound (41 mg). MS 370.2 (M+H); UV 204.2, 269.5, 320.0 nm; t 0.375 min.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-ca682daf38be4922a59191511ef5b6be
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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