4-Methylmorpholine → ((S)-1-{[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-butyl)-carbamic acid tert-butyl ester

HRID 1183021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1183021
[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]([CH2:12][NH2:13])[CH2:9][CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[C:17]([C:24](O)=[O:25])=[N:18][C:19]([Cl:23])=[C:20]([NH2:22])[N:21]=1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]([CH2:12][NH:13][C:24]([C:17]1[C:16]([NH2:15])=[N:21][C:20]([NH2:22])=[C:19]([Cl:23])[N:18]=1)=[O:25])[CH2:9][CH2:10][CH3:11])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 64521193,5-Diamino-6-chloro-pyrazine acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86651886((S)-1-Aminomethyl-butyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 86651887((S)-1-{[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-butyl)-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of ((S)-1-aminomethyl-butyl)-carbamic acid tert-butyl ester (1.70 g, 8.40 mmol), 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid (1.59 g, 8.43 mmol), N-methylmorpholine (3.8 mL, 34.5 mmol) and HATU (3.2 g, 8.42 mmol) in anhydrous DMF (50 mL) is stirred at RT for 16 h. The reaction mixture is concentrated in vacuo and the resulting residue is purified by column chromatography (basic alumina, MeOH:DCM) to afford the title compound as yellow solid. [M+H]+ 333.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe resulting residue is purified by column chromatography (basic alumina, MeOH:DCM)

Quellen und Nachweise

ORD-Eintrag
ord-0cccc2e793234150be418124d328a5fa
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664228B2

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