Acetic Acid → (R)-5-(1-amino-3-cyclopropyl-1-oxopropan-2-ylamino)-3-(thieno[2,3-b]pyridin-3-ylamino)pyrazine-2-carboxamide

HRID 2200412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200412
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:19][C@H:20]([CH2:24][CH:25]2[CH2:27][CH2:26]2)[C:21]([NH2:23])=[O:22])=[N:7][C:8]=1[NH:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[S:12][CH:11]=1)#[N:2].[OH-].[Na+].OO.CC(O)=[O:34]>CCO.CS(C)=O>[NH2:23][C:21](=[O:22])[C@H:20]([NH:19][C:6]1[N:7]=[C:8]([NH:9][C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[S:12][CH:11]=2)[C:3]([C:1]([NH2:2])=[O:34])=[N:4][CH:5]=1)[CH2:24][CH:25]1[CH2:26][CH2:27]1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86685543(R)-2-(5-cyano-6-(thieno[2,3-b]pyridin-3-ylamino)pyrazin-2-ylamino)-3-cyclopropylpropanamide

Produkt 1

HCID 71573436(R)-5-(1-amino-3-cyclopropyl-1-oxopropan-2-ylamino)-3-(thieno[2,3-b]pyridin-3-ylamino)pyrazine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

The compound (R)-2-(5-cyano-6-(thieno[2,3-b]pyridin-3-ylamino)pyrazin-2-ylamino)-3-cyclopropylpropanamide (33 mg, 0.087 mmol) was dissolved in EtOH (2 mL) and DMSO (1 mL), aq. 1N NaOH (1.0 mL) and aq. H2O2 (30%, 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 (34 mg). MS 398.2 (M+H); UV 203.6, 224.8, 262.1, 294.1, 357.3 nm; t 0.532 min.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-2bbe71abe6e64c1ebe7eadec1b971609
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359308B2

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