2,3-Dimethoxyphenethylamine → (E)-3-(6-Amino-pyridin-3-yl)-N-(2,3-dimethoxy-benzyl)-N-methyl-acrylamide

HRID 1362210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1362210
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:4]=1[CH2:5]CN.[CH3:14][NH:15]CC1C=CC2C(=CC=CC=2)C=1CCC.[NH2:30][C:31]1[N:36]=[CH:35][C:34](/[CH:37]=[CH:38]/[C:39]([OH:41])=O)=[CH:33][CH:32]=1.Cl.CN1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1>>[NH2:30][C:31]1[N:36]=[CH:35][C:34](/[CH:37]=[CH:38]/[C:39]([N:15]([CH2:5][C:4]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH3:13])[C:3]=2[O:2][CH3:1])[CH3:14])=[O:41])=[CH:33][CH:32]=1

Komponenten

5

Edukt 4

HCID 1378582,3-DimethoxyphenethylamineHCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acidHCID 59456959Methyl-(1-propyl-naphthalen-2-ylmethyl)amineHCID 66966197(E)-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochloride

Produkt 1

HCID 66967429(E)-3-(6-Amino-pyridin-3-yl)-N-(2,3-dimethoxy-benzyl)-N-methyl-acrylamide

Versuchsvorschrift

According to the procedure of Example 1 (a), except substituting (2,3-dimethoxy-benzyl)methyl-amine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, and substituting (E)-3-(6-amino-pyridin-3-yl)acrylic acid for the (E)-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochloride, the title compound was prepared as a pale yellow solid (434 mg, 53%): 1H NMR (300 MHz, DMSO-d6) δ 8.14 (d, J=11.3 Hz, 1H), 7.89-7.77 (m, 1H), 7.44-7.39 (m, 1H), 7.05-6.94 (m, 3H), 6.68-6.45 (m, 4H), 4.74-4.61 (m, 2H), 3.80 (s, 3H), 3.74 (s, 3H), 3.07-2.86 (m, 3H); MS (ESI) m/e 328 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-d824e0eaee3840ed81fab0774cafe9b3
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879872B2

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