2-(4-Methanesulfonylphenyl)ethan-1-amine → (E)-N-(4-Methanesulfonyl-benzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamide

HRID 1362163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1362163
[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([CH2:9]CN)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:14][NH:15]CC1C=CC2C(=CC=CC=2)C=1CCC.Cl.[O:31]=[C:32]1[NH:41][C:40]2[N:39]=[CH:38][C:37](/[CH:42]=[CH:43]/[C:44]([OH:46])=O)=[CH:36][C:35]=2[CH2:34][CH2:33]1.Cl.CN1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1>>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:15]([CH3:14])[C:44](=[O:46])/[CH:43]=[CH:42]/[C:37]2[CH:38]=[N:39][C:40]3[NH:41][C:32](=[O:31])[CH2:33][CH2:34][C:35]=3[CH:36]=2)=[CH:12][CH:13]=1)(=[O:3])=[O:4]

Komponenten

5

Edukt 4

HCID 27609572-(4-Methanesulfonylphenyl)ethan-1-amineHCID 59456959Methyl-(1-propyl-naphthalen-2-ylmethyl)amineHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid HydrochlorideHCID 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 10023863(E)-N-(4-Methanesulfonyl-benzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamideAusbeute 71 %

Versuchsvorschrift

According to the procedure of Example 1 (a), except substituting (4-methanesulfonyl-benzyl)methylamine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, and substituting (E)-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3yl)acrylic acid hydrochloride 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 (0.400 g, 71%) was prepared as an off-white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.6-10.65 (m, 1H), 8.38-8.34 (m, 1H), 8.10-8.04 (m, 1H), 7.95-7.89 (m, 2H), 7.57-7.46 (m, 3H), 7.28-7.23 (m, 1H), 4.96-4.72 (m, 2H), 3.20-3.16 (m, 5H), 2.94-2.84 (m, 3H) 2.56-2.49 (m, 2H); MS (APCI) m/e 400 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-386fb3bbf8704802961e2e734ad2fa33
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879872B2

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