2-(2-Ethoxy-3-methoxyphenyl)ethanamine → (E)-N-(2-Ethoxy-3-methoxy-benzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamide hydrochloride

HRID 1362207Notes

Reaction equation

HRID 1362207 reaction equation
[ClH:1].[O:2]=[C:3]1[NH:12][C:11]2[N:10]=[CH:9][C:8](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)=[CH:7][C:6]=2[CH2:5][CH2:4]1.Cl.[CH3:19][N:20]1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1.[CH2:37]([O:39][C:40]1[C:48]([O:49][CH3:50])=[CH:47][CH:46]=[CH:45][C:41]=1[CH2:42]CN)[CH3:38].CNCC1C=CC2C(=CC=CC=2)C=1CCC>>[ClH:1].[CH2:37]([O:39][C:40]1[C:48]([O:49][CH3:50])=[CH:47][CH:46]=[CH:45][C:41]=1[CH2:42][N:20]([CH3:19])[C:15](=[O:17])/[CH:14]=[CH:13]/[C:8]1[CH:9]=[N:10][C:11]2[NH:12][C:3](=[O:2])[CH2:4][CH2:5][C:6]=2[CH:7]=1)[CH3:38]

Participants

5

Reactant 4

HCID 47154242-(2-Ethoxy-3-methoxyphenyl)ethanamineHCID 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

Product 1

HCID 10071430(E)-N-(2-Ethoxy-3-methoxy-benzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamide hydrochlorideYield 88%

Procedure

According to the procedure of Example 1, except substituting (E)-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)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, and substituting (2-ethoxy-3-methoxy-benzyl)methylamine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, the title compound (429 mg, 88%) was prepared as an off-white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.6 (s, 1H), 8.34 (d, J=13.2 Hz, 1H), 8.08-8.01 (m, 1H), 7.50 (dd, J=9.2, 2.0 Hz, 1H), 7.25 (dd, J=9.3, 5.5 Hz, 1H), 7.06-6.94 (m, 2H), 6.67 (dd, J=11.4, 4.7 Hz, 1H), 4.91 (br s, 1H), 4.78-4.64 (m, 2H), 4.02-3.95 (m, 2H), 3.79 (s, 3H), 3.09-2.86 (m, 5H), 2.55-2.49 (m, 2H), 1.30-1.26 (m, 3H); MS (ESI) m/e 396 (M+H)+.

Sources & evidence

ORD record
ord-3f1362a09ee14abd858db264c80f1d3f
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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