1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 1-benzyl-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 1670345Notes

Reaction equation

HRID 1670345 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.F[C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1.CCN=C=NCCCN(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:17]([N:18]1[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:2]1=[O:3])[C:16]1[CH:19]=[CH:20][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 673264-FluorobenzylamineHCID 117704Methyl 2-oxo-2H-pyran-3-carboxylate

Product 1

HCID 1478482Methyl 1-benzyl-2-oxo-1,2-dihydropyridine-3-carboxylateYield 79.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A heterogeneous mixture of methyl 2-oxo-2H-pyran-3-carboxylate (Aldrich, 2.0 g, 13 mmol, 1.0 eq) and 4-fluorobenzylamine (1.5 mL, 13 mmol, 1.0 eq) in DMF (10 ml) were stirred at room temperature for 3 h. The reaction mixture was treated with EDCI (3.4 g, 18 mmol, 1.4 eq) and DMAP (0.11 g, 9.91 mmol, 0.07 eq) at room temperature and the resulting solution was stirred for 12 h. The reaction mixture was quenched with 1N aqueous HCl and the solution was extracted with ethyl acetate (4×50 mL). The combined organic extracts were washed with 10% aqueous LiCl (3×70 mL), dried (Na2SO4), filtered and the filtrate concentrated in vacuo to afford the product (2.5 g, 73%) as a solid, that was used without further purification. 1H NMR (DMSO-d6) δ 8.17-8.20 (m, 1H), 8.03-8.05 (m, 1H), 7.38-7.46 (m, 2H), 7.16-7.22 (m, 2H), 6.37 (dd, 1H, J=6.94 Hz), 5.13 (s, 2H), 3.73 (s, 3H); HRMS (ESI+), Calcd.: 262.0879. found: 262.0885.

Workup

  1. stirringthe resulting solution was stirred for 12 h
  2. customThe reaction mixture was quenched with 1N aqueous HCl
  3. extractionthe solution was extracted with ethyl acetate (4×50 mL)
  4. washThe combined organic extracts were washed with 10% aqueous LiCl (3×70 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-07ef93f1e14744778dd9edd88186bd15
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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