Sodium Azide → (R)-N-(1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)-N-methyl-5-(2H-tetrazol-5-yl)pyridin-2-amine

HRID 527933

Reaktionsgleichung

Reaktionsgleichung von HRID 527933
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:14][CH2:13][C@@H:12]([N:15]([CH3:24])[C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][N:17]=3)[CH2:11]2)=[N:3][CH:2]=1.[Cl-].N.[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C)C=O>[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:14][CH2:13][C@@H:12]([N:15]([CH3:24])[C:16]3[CH:23]=[CH:22][C:19]([C:20]4[N:27]=[N:28][NH:29][N:21]=4)=[CH:18][N:17]=3)[CH2:11]2)=[N:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 33557Sodium AzideHCID 20976574Ammonia chlorideHCID 66765754(R)-6-((1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)(methyl)amino)nicotinonitrile

Produkt 1

HCID 86692153(R)-N-(1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)-N-methyl-5-(2H-tetrazol-5-yl)pyridin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of (R)-6-((1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)(methyl)amino)nicotinonitrile (100 mg, 0.3 mmol), ammonia chloride (84 mg, 1.57 mmol) and sodium azide (108 mg, 1.66 mmol) in N,N-dimethylformamide (5.0 mL) was stirred at 120° C. for 16 h. The volatile was removed under vacuum and the residue was purified by chromatography on silica gel to give the title compound. MS (m/z): 363.0 (M+H)+.

Aufarbeitung

  1. customThe volatile was removed under vacuum
  2. customthe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ba07618c7dca45be825a729a72254b9b
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346810B2

Verknüpfte Notizen

Wird geladen…