(3-Chloro-benzofuran-2-ylmethyl)methylamine → (E)-N-(3-Chloro-benzofuran-2-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-acrylamide

HRID 1362368Notes

Reaction equation

HRID 1362368 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[CH:8][C:7]([CH:12]=[CH:13][C:14]([OH:16])=O)=[CH:6][C:5]=2[CH2:4][CH2:3]1.[Cl:17][C:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[O:20][C:19]=1[CH2:27][NH:28][CH3:29]>>[Cl:17][C:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[O:20][C:19]=1[CH2:27][N:28]([CH3:29])[C:14](=[O:16])/[CH:13]=[CH:12]/[C:7]1[CH:8]=[N:9][C:10]2[NH:11][C:2](=[O:1])[CH2:3][CH2:4][C:5]=2[CH:6]=1

Participants

3

Reactant 2

HCID 59277587(3-Chloro-benzofuran-2-ylmethyl)methylamineHCID 66905303(E)-3-(7-oxo-1,5,6,7-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid

Product 1

HCID 16660479(E)-N-(3-Chloro-benzofuran-2-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-acrylamideYield 56%

Procedure

According to the method of example 43d, 3-(7-Oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-acrylic acid (203 mg, 0.8 mmol) and (3-chloro-benzofuran-2-ylmethyl)methylamine (172 mg, 0.88 mmol) were coupled to yield the title compound (176, 56%) as a white solid and as a mixture of amide rotomers. 1H NMR (300 MHz, DMSO-d6) δ 10.63 (s, 1H), 8.40 (s, 1H), 8.09 (s, 1H), 7.21-7.64 (m, 6H), 4.84-5.08 (rotamers, 2s, 2H), 3.22 (s, 3H), 2.91-2.96 (m, 2H), 2.52-2.59 (m, 2H); MS (ESI) m/e 396 (C21H18ClN3O3+H)+.

Sources & evidence

ORD record
ord-6a3504554de74324b4160f142db213cb
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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