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

HRID 347539

反応式

HRID 347539 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-7978079b70154be585257d17e39c7f13
出典データセット
uspto-grants-2007_02
特許番号
US07173031B2

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