Ethyl Acetate → 1-(1-Benzothien-2-ylmethyl)-4-(2-pyridinyl)piperazine

HRID 2377675

Reaktionsgleichung

Reaktionsgleichung von HRID 2377675
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10]O.CS(OS(C)(=O)=O)(=O)=O.CC(=O)OCC.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][N:36]1[CH2:37][CH2:38][N:33]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][N:27]=2)[CH2:34][CH2:35]1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 81560Methanesulfonic anhydrideHCID 944591-(2-Pyridyl)piperazineHCID 27763352-(Hydroxymethyl)benzo[b]thiophene

Produkt 1

HCID 104480641-(1-Benzothien-2-ylmethyl)-4-(2-pyridinyl)piperazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The product from Example 8A (300 mg 1.8 mmol), methane sulfonic anhydride (313 mg, 1.8 mmol), and D1 EA (200 μL 5.4 mmol) were combined. After stirring, 1-(2-pyridinyl)piperazine (328 mg, 2.9 mmol) in 4 ml DCM was also combined and the mixture was processed as described in Example 8B to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.57 (m, 4H) 3.50 (m, 4H) 3.84 (s, 2H) 6.63 (m, 2H) 6.81 (d, J=8.48 Hz, 1H) 7.32 (m, 2H) 7.52 (m, 2H) 7.77 (m, 1H) 7.90 (m, 1H). (ESI) m/z 310 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-2c9d890d88a74dc1afbd3b5f9e8f0caa
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07470691B2

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