Acetic Acid → 6-(1-Carbamoylcyclopentylamino)-5-fluoro-2-(quinolin-3-ylamino)nicotinamide

HRID 84922

Reaktionsgleichung

Reaktionsgleichung von HRID 84922
[C:1]([C:3]1[CH:4]=[C:5]([F:29])[C:6]([NH:20][C:21]2([C:26]([NH2:28])=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22]2)=[N:7][C:8]=1[NH:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)#[N:2].[OH-].[Na+].OO.CC(O)=[O:36]>CCO.CS(C)=O>[C:26]([C:21]1([NH:20][C:6]2[C:5]([F:29])=[CH:4][C:3]([C:1]([NH2:2])=[O:36])=[C:8]([NH:9][C:10]3[CH:11]=[N:12][C:13]4[C:18]([CH:19]=3)=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:7]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1)(=[O:27])[NH2:28]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 675097811-(5-Cyano-3-fluoro-6-(quinolin-3-ylamino)pyridin-2-ylamino)cyclopentanecarboxamide

Produkt 1

HCID 675151346-(1-Carbamoylcyclopentylamino)-5-fluoro-2-(quinolin-3-ylamino)nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of crude 1-(5-cyano-3-fluoro-6-(quinolin-3-ylamino)pyridin-2-ylamino)cyclopentanecarboxamide in EtOH (2 mL) and DMSO (1 mL), aq. 1N NaOH (1 mL) and aq. H2O2 (50%, 1 mL) were added. The mixture was stirred for 1 h. HOAc (0.5 mL) was added. It was concentrated in vacuo. The residue was purified by HPLC to give the titled compound (41 mg). MS 409.4 (M+H); UV 224.1, 243.7, 302.6, 324.8 nm; t 0.495 min.

Aufarbeitung

  1. concentrationIt was concentrated in vacuo
  2. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-62fde1b06d2c4b6c80ab01e03411e537
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846928B2

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