Methyl-(1-propyl-naphthalen-2-ylmethyl)amine → (E)-N-(4-Acetylamino-benzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamide

HRID 1362162Notes

Reaction equation

HRID 1362162 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=CC=CC=2)[C:5]=1CCC.Cl.[O:18]=[C:19]1[NH:28][C:27]2[N:26]=[CH:25][C:24](/[CH:29]=[CH:30]/[C:31]([OH:33])=O)=[CH:23][C:22]=2[CH2:21][CH2:20]1.Cl.CN1CC2C=C(/C=C/C(O)=O)C=NC=2[NH:39][C:38](=[O:52])[CH2:37]1>>[C:38]([NH:39][C:11]1[CH:6]=[CH:5][C:4]([CH2:3][N:2]([CH3:1])[C:31](=[O:33])/[CH:30]=[CH:29]/[C:24]2[CH:25]=[N:26][C:27]3[NH:28][C:19](=[O:18])[CH2:20][CH2:21][C:22]=3[CH:23]=2)=[CH:13][CH:12]=1)(=[O:52])[CH3:37]

Participants

4

Reactant 3

HCID 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 10429735(E)-N-(4-Acetylamino-benzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamideYield 53%

Procedure

According to the procedure of Example 1 (a), except substituting 4-acetamidobenzyl methyl amine 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 (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 (0.283 g, 53%) was prepared as an off-white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.66-10.64 (m, 1H), 9.94-9.92 (m, 1H), 8.36-8.33 (m, 1H), 8.07-8.06 (m, 1H), 7.56-7.48 (m, 3H), 7.33-7.13 (m, 3H), 4.74-4.54 (m, 2H), 3.07-2.86 (m, 5H), 2.53-2.49 (m 2H), 2.01 (s, 3H); MS (ESI) m/e 379 (M+H)+.

Sources & evidence

ORD record
ord-650cc616c5ed4fc6a5a3a406cea3c084
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

Loading…