N-Methylcyclopropanamine → HCID 67774606, compound

HRID 1802305Notes

Reaction equation

HRID 1802305 reaction equation
Br[C:2]1[N:11]=[C:5]2[CH:6]=[C:7]([Br:10])[CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:12][NH:13][CH:14]1[CH2:16][CH2:15]1>>[Br:10][C:7]1[CH:8]=[CH:9][N:4]2[N:3]=[C:2]([N:13]([CH:14]3[CH2:16][CH2:15]3)[CH3:12])[N:11]=[C:5]2[CH:6]=1

Participants

3

Reactant 2

HCID 11029756N-MethylcyclopropanamineHCID 677742742,7-Dibromo[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 67774606HCID 67774606, compoundYield 41%

Procedure

2,7-dibromo-[1,2,4]triazolo[1,5-a]pyridine (1.5 g, 5.42 mmol) was refluxed in N-methylcyclopropanamine (3.85 g, 54.2 mmol) for 4 h. The solvent was evaporated and the residue was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate, filtered and applied on SiO2. Column chromatography over 70 g SiO2 using heptane/ethyl acetate affords (7-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropyl-methyl-amine (593 mg, 41%) as white powder. MS: m/z=397.1 (M+H+).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-47f3d05d3af241739c49032039505ab8
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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