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

HRID 2209044
Notes
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Reaction equation

HRID 2209044 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 62324Propionyl chlorideHCID 1178428716-bromo-2-chloro-N3-methylpyridine-3,4-diamine

Product 1

HCID 117843073N-(6-bromo-2-chloro-3-(methylamino)pyridin-4-yl)propionamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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

  1. customReaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialOrganic phase was dried over Mg2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes