Water → N-(6-bromo-2-chloro-3-(methylamino)pyridin-4-yl)propionamide

HRID 2209044Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH:9][CH3:10])=[C:4]([NH2:11])[CH:3]=1.[C:12](Cl)(=[O:15])[CH2:13][CH3:14].O>N1C=CC=CC=1>[Br:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH:9][CH3:10])=[C:4]([NH:11][C:12](=[O:15])[CH2:13][CH3:14])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

6-bromo-2-chloro-N3-methylpyridine-3,4-diamine 2.59 (410 mg, 2.74 mmol) was dissolved in pyridine (10 mL). Mixture was cooled down to 0° C. and then propanoyl chloride (207 mg) was added portion wise. Mixture was stirred at 0° C. for 1 h. Reaction mixture was poured into water and extracted with ethyl acetate. Organic phase was dried over Mg2SO4, filtered, and concentrated under reduced pressure. Resulting residues were purified by silica gel chromatography (5% MeOH in DCM) to provide N-(6-bromo-2-chloro-3-(methylamino)pyridin-4-yl)propionamide (2.78). LC/MS found for C9H11BrClN3O as (M+H)+ 291.9.

Workup

customReaction mixture
extractionextracted with ethyl acetate
dry with materialOrganic phase was dried over Mg2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customResulting residues were purified by silica gel chromatography (5% MeOH in DCM)

Sources & evidence

ORD record: ord-7dd62089cfbf4dabbcc5445a2b57f6cb
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376441B2

Reaction notes

Loading…