3-Thiophenemethylamine → HCID 68227195, Verbindung

HRID 1186516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186516
CS([C:5]1[N:10]=[C:9]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([N:20]4[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]4)[C:14]3=[N:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[S:27]1[CH:31]=[CH:30][C:29]([CH2:32][NH2:33])=[CH:28]1>>[CH3:26][N:23]1[CH2:24][CH2:25][N:20]([C:19]2[C:14]3[N:15]([C:11]([C:9]4[CH:8]=[CH:7][N:6]=[C:5]([NH:33][CH2:32][C:29]5[CH:30]=[CH:31][S:27][CH:28]=5)[N:10]=4)=[CH:12][N:13]=3)[CH:16]=[CH:17][N:18]=2)[CH2:21][CH2:22]1

Komponenten

3

Edukt 2

HCID 27763813-ThiophenemethylamineHCID 682264863-(2-Methanesulfonyl-pyrimidin-4-yl)-8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazine

Produkt 1

HCID 68227195HCID 68227195, VerbindungAusbeute 53 %

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

The mixture of 3-(2-methanesulfonyl-pyrimidin-4-yl)-8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazine (from Example 46 supra) (120 mg, 0.32 mmol) and thiophen-3-ylmethanamine (145 mg, 1.28 mmol) was heated at 140° C. with stirring for 2 hours. The oil was purified by chromatography (silica gel, 10 g, 200-300 mesh, eluting with dichloromethane:methanol, 30:1 to 10:1) to afford {4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-thiophen-3-ylmethyl-amine (Yield 69 mg, 52.8%). 1H NMR (300 MHz, DMSO-d6): δ 8.41 (s, 1H), 8.35 (d, 1H, J=5.4 Hz), 7.94 (t, 1H, J=5.7 Hz), 7.51-7.34 (m, 3H), 7.20-7.12 (m, 2H), 4.56 (d, 2H, J=5.7 Hz), 4.17 (brs, 4H), 2.52-2.44 (m, 4H), 2.23 (s, 3H). LC-MS: [M+H]+ 407.

Aufarbeitung

  1. customThe oil was purified by chromatography (silica gel, 10 g, 200-300 mesh, eluting with dichloromethane:methanol, 30:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-5728df290d214b1baa15c9f827dec9a3
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673905B2

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