3-Methoxybenzylamine → N-[(3-methoxyphenyl)methyl]-1,6-naphthyridine-2-carboxamide

HRID 1861810

반응식

HRID 1861810 반응식
[N:1]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.O.ON1C2C=CC=CC=2N=N1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][NH2:31]>CN(C=O)C>[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][NH:31][C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[N:7][CH:6]=2)[N:1]=1)=[O:13]

참가 물질

5

반응물 3

HCID 211563-MethoxybenzylamineHCID 7359081,6-Naphthyridine-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 484991N-[(3-methoxyphenyl)methyl]-1,6-naphthyridine-2-carboxamide수율 94%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirring mixture of 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol) in anhydrous DMF (1.0 mL) at room temperature was added sequentially 1-hydroxybenzotriazole hydrate (42.7 mg, 0.316 mmol), 3-methoxybenzylamine (56.6 μL, 0.431 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarboiimide hydrochloride (61.8 mg, 0.316 mmol). The resulting mixture was allowed to stir at room temperature overnight and it was found to be clear. The solvent was removed under vacuum. Flash column chromatography of the residue (50% hexane/ethyl acetate to 100% ethyl acetate) afforded the desired product as a clear oil (79.1 mg, 94%).

후처리

  1. customThe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-18e797cf2c1444ed977b78aacd7a1433
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06534520B2

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