Acetyl chloride → Ethyl {4-[2-(allyloxy)-4-methylphenyl]-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl}(oxo)acetate hydrochloride salt

HRID 63960

Reaktionsgleichung

[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[C:12]([C:14]1[C:18]2[CH2:19][CH2:20][CH2:21][CH2:22][C:17]=2[S:16][C:15]=1[NH2:23])=O)[CH:2]=[CH2:3].[O:24]=[C:25]([CH2:31][C:32](=O)[CH3:33])[C:26]([O:28][CH2:29][CH3:30])=[O:27].C([Cl:38])(=O)C>C(O)C>[ClH:38].[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[C:12]1[C:31]([C:25](=[O:24])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:32]([CH3:33])[N:23]=[C:15]2[S:16][C:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=3[C:14]=12)[CH:2]=[CH2:3]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a stirred solution of [2-(allyloxy)-4-methylphenyl](2-amino-4,5,6,7-tetrahydro-1-benzothieno-3-yl)methanone (Step 5, 882 mg, 2.69 mmol) in ethanol (30 mL) was added ethyl 2,4-dioxopentanoate (378 μL, 2.69 mmol) followed by acetyl chloride (766 μL, 10.8 mmol), and the reaction was heated to 50° C. for 1 hour. The reaction was then concentrated in vacuo to give a mixture of diastereoisomers of the title compound as the hydrochloride salt, as a pale yellow oil, 1 g, in an 86% yield. LCMS (2 min acidic) 1.70 min 54-100% pure by UV, ES+/AP+ 450. 1HNMR (400 MHz, CDCl3) δ ppm 1.12 (t, 3H), 1.55-1.70 (m, 2H), 1.78-1.89 (m, 2H), 1.92-2.08 (m, 2H), 2.43 (, 3H), 2.87-2.93 (m, 2H), 2.95 (s, 3H), 3.84-3.94 (m, 2H), 4.39-4.51 (m, 2H), 5.09-5.20 (m, 2H), 5.82 (m, 1H), 6.76 (s, 1H), 6.87 (d, 1H), 6.95 (d, 1H).

Aufarbeitung

concentrationThe reaction was then concentrated in vacuo
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Quellen und Nachweise

ORD-Eintrag: ord-241031f2ad7b4a0cbb754c1dbfe9e302
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09447116B2

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