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

HRID 1362206Notes

Reaction equation

HRID 1362206 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.[CH:37]([O:40][C:41]1[C:49]([O:50][CH3:51])=[CH:48][CH:47]=[CH:46][C:42]=1[CH2:43]CN)([CH3:39])[CH3:38].CNCC1C=CC2C(=CC=CC=2)C=1CCC>>[ClH:1].[CH:37]([O:40][C:41]1[C:49]([O:50][CH3:51])=[CH:48][CH:47]=[CH:46][C:42]=1[CH2:43][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])[CH3:39]

Participants

5

Reactant 4

HCID 12176049(2-Isopropoxy-3-methoxy-benzyl)methylamineHCID 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 10049194(E)-N-(2-Isopropoxy-3-methoxy-benzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamide hydrochlorideYield 83%

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-isopropoxy-3-methoxy-benzyl)methylamine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, the title compound (326 mg, 83%) was prepared as a white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.6 (s, 1H), 8.36 (d, J=17.3 Hz, 1H), 8.10-7.98 (m, 1H), 7.50 (d, J=15.3 Hz, 1H), 7.28-7.17 (m, 1H), 7.05-6.93 (m, 2H), 6.63 (dd, J=7.3, 7.3 Hz, 1H), 5.77 (br s, 1H), 4.77-4.63 (m, 2H), 4.59-4.45 (m, 1H), 3.79 (s, 3H), 3.08-2.81 (m, 5H), 2.56-2.44 (m, 2H), 1.23 (t, J=5.7 Hz, 6H); MS (ESI) m/e 410 (M+H)+.

Sources & evidence

ORD record
ord-890c34b905d3420e8c6166af2dbafa3d
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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