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

HRID 2117145Notes

Reaction equation

HRID 2117145 reaction equation
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

Participants

6

Reactant 3

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

Product 1

HCID 21081726Methyl 2-oxo-1-(pyridin-2-yl)-1,2-dihydropyridine-3-carboxylateYield 72.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-4568ac5b129f4a52bed348d09b75bd40
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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