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

HRID 347540노트

반응식

HRID 347540 반응식
O=[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][O:3]1.N[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.CC[N:21]=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:21]1[C:16]1[CH:17]=[CH:18][CH:13]=[CH:14][N:15]=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 21081726Methyl 2-oxo-1-(pyridin-2-yl)-1,2-dihydropyridine-3-carboxylate수율 72.4%

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 at rt for 12 h and treated with EDCI.HCl (650 mg, 3.4 mmol) and DMAP (200 mg). The reaction mixture was stirred for 2.5 days at rt, and most of the DMF was removed in vacuo. The residue was purified by preparative HPLC to afford the desired product (500 mg, 72%) as a glassy material. 1H NMR (CDCl3) δ 8.53 (d, 1H, J=5.0 Hz), 8.20 (dd, 1H, J=9.2, 2.2 Hz), 8.06 (dd, 1H, J=6.0, 1.1 Hz), 7.89–7.82 (m, 2H), 7.32 (dd, 1H, J=6.6, 5.0 Hz), 6.36 (t, 1H, J=6.6 Hz), 3.86 (s, 3H); MS(ESI+) m/z 231.2 (M+H)+.

후처리

  1. stirringThe reaction mixture was stirred for 2.5 days at rt
  2. custommost of the DMF was removed in vacuo
  3. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-2e3a6493ad854b05b7f49e29a62bab58
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173031B2

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