(S)-1-(4-Fluorophenyl)-ethylamine → (S)-N2-(5-Cyclopropyl-1H-pyrazol-3-yl)-3-fluoro-N6-(1-(4-fluorophenyl)ethyl)pyridine-2,6-diamine

HRID 75901

Reaktionsgleichung

Reaktionsgleichung von HRID 75901
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[N:15]=[C:14]([NH:16][C@H:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH3:18])[C:13](N)=[CH:12][CH:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[F:27]C1C=CC([C@@H](N)C)=CC=1>>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:11]([F:27])=[CH:12][CH:13]=[C:14]([NH:16][C@H:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH3:18])[N:15]=3)[CH:5]=2)[CH2:3][CH2:2]1

Komponenten

3

Edukt 2

HCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 68521442(S)-N6-(5-Cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(4-fluorophenyl)ethyl)pyridine-2,3,6-triamine

Produkt 1

HCID 69286268(S)-N2-(5-Cyclopropyl-1H-pyrazol-3-yl)-3-fluoro-N6-(1-(4-fluorophenyl)ethyl)pyridine-2,6-diamineAusbeute 26,8 %

Reaktionsbedingungen

Temperatur
185 °C

Versuchsvorschrift

A mixture of N-(5-cyclopropyl-1H-pyrazol-3-yl)-3,6-difluoropyridin-2-amine (Method 31, 0.10 g, 0.42 mmol) and (S)-1-(4-fluorophenyl)ethanamine (0.3 g, 2.2 mmol) were heated to 185° C. under microwave conditions (30 min×3 cycles). The resulting dark oil was purified by column chromatography (DCM-MeOH=80:1) to give the title compound (0.04 g, 26%). 1H NMR (400 MHz, CD3OD) δ 7.08-6.99 (m, 3H), 6.67-6.62 (m, 2H), 6.22 (dd, J=8.9, 2.3 Hz, 1H), 5.04 (s, 1H), 4.64-4.59 (m, 1H), 1.16-1.12 (m, 4H), 0.30-0.14 (m, 3H), 0.04-0.02 (m, 1H). MS: Calcd.: 355. Found: [M+H]+ 356.

Aufarbeitung

  1. customThe resulting dark oil was purified by column chromatography (DCM-MeOH=80:1)

Quellen und Nachweise

ORD-Eintrag
ord-66b7c74964da4b53ad429ab8d96abea1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835465B2

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