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 63946

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

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a stirred solution of (2-allyloxy-4-methyl-phenyl)-(2-amino-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)-methanone (882 mg, 2.69 mmols) in ethanol (30 mL) was added ethyl 2,4-dioxopentanoate (426 mg, 378 μL, 1 eq) followed by acetyl chloride (846 mg, 766 μL, 4 eq), and the reaction was heated to 50° C. for 1 hour. The reaction was then concentrated in vacuo to give [4-(2-allyloxy-4-methyl-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl]-oxo-acetic acid ethyl ester hydrochloride as a pale yellow oil 1 g (86% yield). LCMS (2 min acidic) 1.70 min 54-100% pure by UV, ES+/AP+ 450. HNMR (CDCl3)>90% pure 6.95 (d, J=7.0 Hz, 1 H) 6.87 (d, J=7.0 Hz, 1 H) 6.76 (s, 1 H) 5.82 (m, 1 H) 5.09-5.20 (m, 2 H) 4.39-4.51 (m, 2 H) 3.84-3.94 (m, 2 H) 2.95 (s, 3 H) 2.87-2.93 (m, 2 H) 2.43 (s, 3 H) 1.92-2.08 (m, 2 H) 1.78-1.89 (m, 2 H) 1.55-1.70 (m, 2 H) 1.12 (t, J=7.1 Hz, 3 H).

Aufarbeitung

concentrationThe reaction was then concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-b09bca89777d4cdf81d79a917a500226
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09447116B2

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