Ethyl Acetate → N-{4-[6-(3,4,5-trimethoxyphenylamino)pyrazin-2-yloxy]naphthalen-1-yl}acetamide

HRID 16272

Reaktionsgleichung

Reaktionsgleichung von HRID 16272
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[CH:19]=[N:18][CH:17]=[C:16](Cl)[N:15]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[OH:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([NH:32][C:33](=[O:35])[CH3:34])=[CH:24][CH:23]=1.C(OCC)(=O)C>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[N:15]=[C:16]([O:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]([NH:32][C:33](=[O:35])[CH3:34])=[CH:24][CH:23]=3)[CH:17]=[N:18][CH:19]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 235848N-(4-hydroxynaphthalen-1-yl)acetamideHCID 116090492-(3,4,5-Trimethoxyphenylamino)-6-chloropyrazine

Produkt 1

HCID 24879328N-{4-[6-(3,4,5-trimethoxyphenylamino)pyrazin-2-yloxy]naphthalen-1-yl}acetamideAusbeute 6,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Using Method X, with 200 mg of 2-(3,4,5-trimethoxyphenylamino)-6-chloropyrazine (all amounts scaled accordingly) and N-(4-hydroxynaphthalen-1-yl)acetamide (CJS 704), using an identical workup and chromatography using a mixture of ethyl acetate and dichloromethane (7:3) furnished 31 mg of the title compound. Yield: 6.7%. 1H NMR (250 MHz, DMSO-d6) δ 2.21 (s, 3H), 3.20 (s, 9H), 3.48 (s, 3H), 6.61 (s, 2H), 7.31 (d, 1H, J=8.2 Hz), 7.59 (t, 2H, J=7.6 Hz), 7.70 (d, 1H, J=8.3 Hz), 7.91 (s, 1H), 7.96-7.99 (m, 2H), 8.13 (d, 1H, J=7.8 Hz), 9.49 (s, 1H), 9.93 (s, 1H). 13C NMR (62.5 MHz, DMSO-d6) δ 23.44, 55.10, 59.95, 95.38, 116.77, 120.89, 121.48, 121.61, 123.18, 126.38, 126.53, 127.11, 128.23, 128.71, 130.90, 131.98, 136.18, 146.44, 150.64, 152.59, 158.26, 168.93. m/z [(M+H)+ calcd for C25H24N4O5 460.2].

Quellen und Nachweise

ORD-Eintrag
ord-0d828a3c958f4f30accdfa1d0533a0ac
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737152B2

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