Triethylamine → HCID 45867410, compound

HRID 2353388Notes

Reaction equation

HRID 2353388 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][N:4]=1.Cl.[CH3:13][NH:14][O:15][CH3:16].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>CN(C=O)C.ON1C2N=CC=CC=2N=N1>[CH3:13][N:14]([O:15][CH3:16])[C:7]([C:6]1[CH:5]=[N:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=1)=[O:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 5924996-Methoxynicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 45867410HCID 45867410, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 181649HOAtCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-methoxynicotinic acid (0.784 g) in DMF (10 ml) was stirred with N,O-dimethylhydroxylamine hydrochloride (0.5 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.16 g) and 1-hydroxy-7-azabenzotriazole (50 mg). Triethylamine (1.67 ml) was added and the reaction mixture was stirred at room temperature for 18 h. The solvent was removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was separated using a hydrophobic filter tube and the solvent was evaporated to give the title compound as a colourless oil (0.86 g).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c48847ddfd1e483386d7a942113bd4e6
Source dataset
uspto-grants-2010_07
Patent number
US07750026B2

Reaction notes

Loading…