1,2-Dichloroethane → (E)-3-(6,6-dimethyl-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)acrylamide

HRID 1362460Notes

Reaction equation

C(Cl)CCl.Cl.[CH3:6][C:7]1([CH3:23])[C:16](=[O:17])[NH:15][C:14]2[N:13]=[CH:12][C:11](/[CH:18]=[CH:19]/[C:20]([OH:22])=O)=[CH:10][C:9]=2[CH2:8]1.C1C=CC2N(O)N=NC=2C=1.[CH3:34][NH:35][CH2:36][C:37]1[O:38][C:39]2[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=2[C:41]=1[CH3:42].C(N(C(C)C)C(C)C)C>CN(C=O)C.O>[CH3:23][C:7]1([CH3:6])[C:16](=[O:17])[NH:15][C:14]2[N:13]=[CH:12][C:11](/[CH:18]=[CH:19]/[C:20]([N:35]([CH3:34])[CH2:36][C:37]3[O:38][C:39]4[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=4[C:41]=3[CH3:42])=[O:22])=[CH:10][C:9]=2[CH2:8]1

Participants

Conditions

Temperature: 40 °C

Procedure

EDC (102 mg, 0.53 mmol) was added to a suspension of (E)-3-(6,6-dimethyl-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride (125 mg, 0.44 mmol), HOBt (66 mg, 0.49 mmol), N-methyl(3-methylbenzofuran-2-yl)methanamine (92 mg, 0.49 mmol) and (i-Pr)2EtN (0.37 mL, 2.2 mmol) in DMF (5 mL). The mixture was allowed to stir for 23 h at 40° C. The mixture was cooled to room temperature and diluted with water (20 mL) at 0° C. to yield a brown precipitate, which was collected by suction filtration. The solid was then triturated with diethyl ether to obtain an off-white solid product. Yield: 137 mg (81%); 1H NMR (300 MHz, DMSO-d6) δ 10.64 (s, 1H), 8.40 (s, 1H), 8.09 (s, 1H), 7.59-7.19 (m, 6H), 4.91 (s, 2H), 3.09 (s, 3H), 2.81 (s, 2H), 2.28 (s, 3H),1.09 (s, 6H); ESI MS m/z 404 [C24H25N3O3+H]+.

Workup

temperatureThe mixture was cooled to room temperature
customto yield a brown precipitate, which
filtrationwas collected by suction filtration
customThe solid was then triturated with diethyl ether
customto obtain an off-white solid product

Sources & evidence

ORD record: ord-8c19166b0bbd400481dd3899bfed3198
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879872B2

Reaction notes

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