3-Aminopyridine → Methyl 2-oxo-1-(pyridin-3-yl)-1,2-dihydropyridine-3-carboxylate

HRID 347539

반응식

HRID 347539 반응식
O=[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][O:3]1.[NH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.CN(C1C=CN=CC=1)C>[O:3]=[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][N:12]1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1

참가 물질

6

반응물 3

HCID 100093-AminopyridineHCID 117704Methyl 2-oxo-2H-pyran-3-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 21081727Methyl 2-oxo-1-(pyridin-3-yl)-1,2-dihydropyridine-3-carboxylate수율 141.9%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of methyl 2-oxo-2H-pyran-3-carboxylate (462 mg, 3 mmol, Aldrich) in DMF (6 mL) at rt was added 3-aminopyridine (282 mg, 3 mmol). The reaction mixture was stirred overnight at rt, treated with EDCI.HCl (650 mg, 3.4 mmol) and DMAP (200 mg), stirred for an additional 24 h, and concentrated in vacuo. The residue was purified by preparative HPLC to afford the desired product (980 mg, 95%) as a beige solid. 1H NMR (CDCl3) δ 13.00 (br s, 1H), 8.83 (br s, 1H), 8.74 (br s, 1H), 8.29 (dd, 1H, J=7.2, 1.7 Hz), 8.18 (d, 1H, J=8.3 Hz), 7.73 (dd, 1H, J=7.7, 5.0 Hz), 7.66 (dd, 1H, J=6.6, 1.6 Hz), 6.42 (t, 1H, J=7.1 Hz), 3.87 (s, 3H).

후처리

  1. stirringstirred for an additional 24 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-7978079b70154be585257d17e39c7f13
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173031B2

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