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

HRID 2200425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200425
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-74a4373be60e4f948f1c33612f5a690c
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359308B2

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