Triethylamine → 5-Bromo-3-((2-(4-methylpiperazin-1-yl)ethylamino)methyl)pyridin-2-amine

HRID 633976

Reaktionsgleichung

C(N(CC)CC)C.Br.[NH2:9][C:10]1[N:17]=[CH:16][C:15]([Br:18])=[CH:14][C:11]=1[CH:12]=O.[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][NH2:28])[CH2:22][CH2:21]1.[BH4-].[Na+]>CO>[Br:18][C:15]1[CH:14]=[C:11]([CH2:12][NH:28][CH2:27][CH2:26][N:23]2[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]2)[C:10]([NH2:9])=[N:17][CH:16]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Triethylamine (1.0 mL, 7.09 mmol) was added to a solution of 2-amino-5-bromonicotinaldehyde hydrobromide (1.0 g, 3.54 mmol) in methanol (24 mL) at room temperature. The reaction mixture was stirred for 10 minutes prior to the addition of 2-(4-methylpiperazin-1-yl)ethanamine (558 mg, 3.90 mmol). The reaction mixture was then stirred overnight and cooled to 0° C. Sodium borohydride (201 mg, 5.32 mmol) was added portionwise at 0° C. and the reaction mixture was allowed to reach room temperature and stirred for 4 hours. After concentration to dryness, the residue was purified by chromatography on silica gel using dichloromethane/methanol/ammoniac (10:0:0.1 to 9:1:0.1) as eluent. The title product was obtained as a yellow solid (560 mg, 48%).

Aufarbeitung

stirringThe reaction mixture was then stirred overnight
customto reach room temperature
stirringstirred for 4 hours
concentrationAfter concentration to dryness
customthe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-42bfe850ccd542f5893df646b6f5d588
Quelldatensatz: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09321769B2

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