3-(4-Methylpiperazin-1-yl)aniline → N(8)-(2-Methoxy-benzyl)-N(2)-[3-(4-methyl-piperazin-1-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

HRID 472644

Reaktionsgleichung

Reaktionsgleichung von HRID 472644
Cl[C:2]1[N:20]=[C:5]2[C:6]([NH:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][CH3:19])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[C:30]([CH:32]=[CH:33][CH:34]=2)[NH2:31])[CH2:24][CH2:23]1>>[CH3:19][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][NH:10][C:6]1[C:5]2[N:4]([N:3]=[C:2]([NH:31][C:30]3[CH:32]=[CH:33][CH:34]=[C:28]([N:25]4[CH2:24][CH2:23][N:22]([CH3:21])[CH2:27][CH2:26]4)[CH:29]=3)[N:20]=2)[CH:9]=[CH:8][CH:7]=1

Komponenten

3

Edukt 2

HCID 115646133-(4-Methylpiperazin-1-yl)anilineHCID 67479414(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(2-methoxy-benzyl)-amine

Produkt 1

HCID 59612333N(8)-(2-Methoxy-benzyl)-N(2)-[3-(4-methyl-piperazin-1-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

Versuchsvorschrift

N(8)-(2-Methoxy-benzyl)-N(2)-[3-(4-methyl-piperazin-1-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine was prepared from (2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(2-methoxy-benzyl)-amine (100.00 mg, 0.34634 mmol) and 3-(4-methylpiperazin-1-yl)aniline (74.2 mg, 0.388 mmol) in a manner analogous to Example 2d. Product isolated as a brown foam (39.14 mg, 25.4%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.12 (s, 1H), 7.96 (d, J=6.4 Hz, 1H), 7.25 (m, 4H), 7.09 (t, J=15.9, 7.8 Hz, 1H), 7.03 (d, J=8.6 Hz, 1H), 6.88 (t, J=15.0, 7.9 Hz, 1H), 6.73 (t, J=14.5, 7.4 Hz, 1H) 6.46 (d, J=8.6 Hz, 1H), 6.32 (d, J=8.1 Hz, 1H), 6.10 (m, 1H), 4.48 (d, J=5.2 Hz, 2H), 3.87 (s, 3H), 3.12 (s, 4H), 2.45 (s, 4H), 2.22 (s, 3H). MS=444 (MH)+.

Quellen und Nachweise

ORD-Eintrag
ord-5f30f88a04dd461ea6de0d49f726feb2
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633173B2

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