1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N,2-Dimethoxy-N-methylnicotinamide

HRID 1037239Notes

Reaction equation

HRID 1037239 reaction equation
[CH3:1][O:2][C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.Cl.[CH3:13][O:14][NH:15][CH3:16].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([N:15]([O:14][CH3:13])[CH3:16])=[O:7]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 7080932-Methoxynicotinic acid

Product 1

HCID 45871212N,2-Dimethoxy-N-methylnicotinamideYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred ice-cooled mixture of 2-methoxy-nicotinic acid (1.43 g, 9.31 mmol) and O,N-dimethyl-hydroxylamine hydrochloride (1.0 g, 10.3 mmol) in DCM (50 mL) was added DIPEA (6.4 mL, 37.3 mmol). EDCI (2.14 g, 11.1 mmol) was added portionwise over 5 minutes. After 18 hours, the reaction mixture was washed successively with saturated sodium bicarbonate and water. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 50 to 75% EtOAc in cyclohexane) to afford the title compound (0.92 g, 51%) as a colourless oil. LCMS (Method A): RT=2.48 min, [M+H]+=197.

Workup

  1. washthe reaction mixture was washed successively with saturated sodium bicarbonate and water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2314540807074efaa11eb8bd1ee3643e
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

Loading…