Pyridine → HCID 22185459, compound

A suspension of 4-chloro-3-methoxybenzoic acid (F. Claudi et al J. Med. Chem., 1992, 35, 4408) (37.2 g, 0.2 mol) in dichloromethane (500 ml) containing oxalyl chloride (26 ml) was treated with N,N-dimethylformamide (10 drops). After stirring at room temperature for 6 hours the solution was concentrated at reduced pressure, additional dichloromethane was added to the residue and the solvent was re-evaporated. The residue was then dissolved in acetonitrile (600 ml) and methoxymethylamine hydrochloride (20.5 g, 0.21 mol) added. The mixture was cooled in an ice-bath, a solution of pyridine (80 ml) in acetonitrile (150 ml) added dropwise, and the mixture stirred at room temperature for 18 hours. The solution was concentrated and the residue partitioned between ethyl acetate and saturated potassium carbonate solution. The organic layer was separated, washed with brine, dried (MgSO4) and concentrated at reduced pressure to give the title compound (40.0 g, 87%) as a colourless oil; MS(ES+) m/e 230/232 [M+H]+.

1. concentrationwas concentrated at reduced pressure, additional dichloromethane
2. additionwas added to the residue
3. customthe solvent was re-evaporated
4. dissolutionThe residue was then dissolved in acetonitrile (600 ml)
5. temperatureThe mixture was cooled in an ice-bath
6. stirringthe mixture stirred at room temperature for 18 hours
7. concentrationThe solution was concentrated
8. customthe residue partitioned between ethyl acetate and saturated potassium carbonate solution
9. customThe organic layer was separated
10. washwashed with brine
11. dry with materialdried (MgSO4)
12. concentrationconcentrated at reduced pressure

ORD record

ord-f261d622096b4fbd90a7e723078918cf

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06987119B2