4-Methoxybenzylamine → (4-Methoxy-benzyl)-[1,5]naphthyridin-4-yl-amine

HRID 513750Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.Cl[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][N:20]=2)[N:15]=[CH:14][CH:13]=1>CCCCO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][N:20]=3)[N:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 150 °C

Procedure

p-Methoxybenzylamine (1.45 g, 10.6 mmol) was added to a solution of 4-chloro-[1,5]naphthyridine 484 (0.35 g, 2.13 mmol) in n-BuOH (9 ml) and the mixture was heated at 150° C. for 18 h. The solvent was removed in vacuo. The crude residue was purified by column chromatography with n-hexane/EtOAc (80:20) as the eluent to give the title compound (0.5 g, 89%).

Workup

customThe solvent was removed in vacuo
customThe crude residue was purified by column chromatography with n-hexane/EtOAc (80:20) as the eluent

Sources & evidence

ORD record: ord-9ec5792581e040ae82a16fddb93ccc43
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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