2,3-Dimethylbenzeneethanamine → (E)-N-(2,3-Dimethyl-benzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamide

HRID 1362166Notes

Reaction equation

HRID 1362166 reaction equation
CC1C(C)=CC=CC=1CCN.[CH3:12][NH:13][CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18]C=CC=2)[C:16]=1[CH2:25]CC.Cl.[O:29]=[C:30]1[NH:39][C:38]2[N:37]=[CH:36][C:35](/[CH:40]=[CH:41]/[C:42](O)=[O:43])=[CH:34][C:33]=2[CH2:32][CH2:31]1.Cl.CN1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1>>[CH3:25][C:16]1[C:17]([CH3:18])=[CH:22][CH:23]=[CH:24][C:15]=1[CH2:14][N:13]([CH3:12])[C:42](=[O:43])/[CH:41]=[CH:40]/[C:35]1[CH:36]=[N:37][C:38]2[NH:39][C:30](=[O:29])[CH2:31][CH2:32][C:33]=2[CH:34]=1

Participants

5

Reactant 4

HCID 223795192,3-DimethylbenzeneethanamineHCID 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 9997959(E)-N-(2,3-Dimethyl-benzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamideYield 75%

Procedure

According to the procedure of Example 1 (a), except substituting 2,3-dimethylbenzylmethyl 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 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 (0.368 g, 75%) was prepared as an off-white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.68-10.64 (m, 1H), 8.38-8.32 (m, 1H), 8.10-7.99 (m, 1H), 7.57-7.50 (m, 1H), 7.29-7.04 (m, 3H), 6.94-6.77 (m, 1H), 4.82-4.65 (m, 2H), 3.06-2.85 (m, 5H), 2.57-2.48 (m 2H), 2.28-2.14 (m, 6H); MS (APCI) m/e 350 (M+H)+.

Sources & evidence

ORD record
ord-249d238d12d849c0b0af70bf00866ad8
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

Loading…