2-Methoxy-N-methyl-1-naphthalenemethanamine → (E)-N-(2-Methoxy-naphthalen-1-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamide

HRID 1362164Notes

Reaction equation

HRID 1362164 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH2:13][NH:14][CH3:15].CNCC1C=CC2C(=CC=CC=2)C=1CCC.Cl.[O:33]=[C:34]1[NH:43][C:42]2[N:41]=[CH:40][C:39](/[CH:44]=[CH:45]/[C:46]([OH:48])=O)=[CH:38][C:37]=2[CH2:36][CH2:35]1.Cl.CN1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1>>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH2:13][N:14]([CH3:15])[C:46](=[O:48])/[CH:45]=[CH:44]/[C:39]1[CH:40]=[N:41][C:42]2[NH:43][C:34](=[O:33])[CH2:35][CH2:36][C:37]=2[CH:38]=1

Participants

5

Reactant 4

HCID 5983882-Methoxy-N-methyl-1-naphthalenemethanamineHCID 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 10408748(E)-N-(2-Methoxy-naphthalen-1-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamideYield 71%

Procedure

According to the procedure of Example 1 (a), except substituting (2-methoxy-naphthalen-1-ylmethyl)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 (0.403 g, 71%) was prepared as an orange-brown solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.66 (s, 1H), 8.37 (s, 1H), 8.08-7.81 (m, 4H), 7.70-7.11 (m, 5H), 5.22-5.09 (m, 2H), 3.98-3.90 (m, 3H), 2.91-2.87 (m, 5H), 2.63-2.49 (m, 2H); MS (ESI) m/e 402 (M+H)+.

Sources & evidence

ORD record
ord-1683318d6ba84c71aabba56000af6567
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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