Triethylamine → HCID 87085130, Verbindung

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Reaktionsgleichung

ClC1C=[CH:5][S:4][C:3]=1C(OC)=O.[CH3:11][NH:12][C:13]1[S:14][C:15]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[N:16][N:17]=1.C(OCC)(=[O:26])C.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClC(Cl)C.CCCCCC>[CH3:11][N:12]([C:13]1[S:14][C:15]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[N:16][N:17]=1)[C:5](=[O:26])[S:4][CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

4-Dimethylaminopyridine (81 mg, 0.66 mmol, 1.5 equiv) and methyl chlorothiolformate (50 μL, 0.57 mmol, 1.3 equiv) were sequentially added to a stirred suspension of N-methyl-5-(pyridin-3-yl)-1,3,4-thiadiazol-2-amine (85 mg, 0.44 mmol, 1.0 equiv) in dichloroethane (3.4 mL) at 23° C. The resulting solution was heated to 75° C. and stirred for 72 h. The cooled reaction mixture was directly subjected to silica gel column chromatography (55% ethyl acetate in hexane spiked with 5% triethylamine) to afford the title compound as an off-white powder (100 mg, 83%): mp 192-194° C.; IR (KBr thin film) 2931 (w), 1727 (w), 1634 (s), 1570 (w) cm−1; 1H NMR (300 MHz, CDCl3) δ 9.13 (d, J=2 Hz, 1H), 8.70 (dd, J=5, 2 Hz, 1H), 8.28 (dt, J=8, 2 Hz, 1H), 7.43 (dd, J=8, 5 Hz, 1H), 3.86 (s, 3H), 2.53 (s, 3H); ESIMS m/z 267 ([M+H]+). Compound 87 was prepared as described in Example 15.

Aufarbeitung

customThe cooled reaction mixture

Quellen und Nachweise

ORD-Eintrag: ord-3a4f2c5c185e4567898f73b12d470971
Quelldatensatz: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08912338B2

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