Cyclopropylamine → N-[5-(cyclopropylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide

HRID 2382814Notes

Reaction equation

HRID 2382814 reaction equation
Br[C:2]1[N:7]2[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH:20]1([NH2:23])[CH2:22][CH2:21]1>O>[CH:20]1([NH:23][C:2]2[N:7]3[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]4[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=4)[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 25212514N-(5-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide

Product 1

HCID 59437438N-[5-(cyclopropylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(5-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide ((B2), 50 mg; 0.16 mmol; 1.0 eq.) in cyclopropylamine (1 mL) was heated at 80° C. overnight. The reaction mixture was diluted with H2O and extracted with EtOAc. Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated. The title compound was obtained by recrystallization in EtOAc/c-Hex as a white powder (16.60 mg; 35%). HPLC, Rt: 1.77 min. (purity 98.3%). LC/MS, M+(ESI): 295.4, M−(ESI): 293.4.

Workup

  1. extractionextracted with EtOAc
  2. washCombined organic phases were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8c3705aac10f499993efd8c01c83d8b7
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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