Cyclobutylamine → N-[7-chloro-5-(cyclobutylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide

HRID 2382888Notes

Reaction equation

HRID 2382888 reaction equation
Cl[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]=[C:4]([Cl:20])[CH:3]=1.[CH:21]1([NH2:25])[CH2:24][CH2:23][CH2:22]1>>[Cl:20][C:4]1[CH:3]=[C:2]([NH:25][CH:21]2[CH2:24][CH2:23][CH2:22]2)[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]=1

Participants

3

Reactant 2

HCID 75645CyclobutylamineHCID 25212768N-(5,7-dichloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide

Product 1

HCID 59437448N-[7-chloro-5-(cyclobutylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamideYield 21%

Conditions

Temperature
180 °C

Procedure

The title compound was prepared following procedure described for example 84, but starting from N-(5,7-dichloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide ((B10), 100 mg; 0.32 mmol; 1.0 eq) and cyclobutylamine (139 μL; 1.62 mmol; 5.0 eq) heated at 180° C. for 1800 s after which solvents were evaporated under vacuum, then resuspended in water, filtered and washed with EtOAc to give the title compound as a white solid (23 mg, 21%). HPLC, Rt: 2.95 min. (purity 96.7%). LC/MS, M+(ESI): 342.8, M−(ESI): 340.9.

Workup

  1. customThe title compound was prepared following procedure
  2. customwere evaporated under vacuum
  3. filtrationfiltered
  4. washwashed with EtOAc

Sources & evidence

ORD record
ord-9fe787a7fc5f44d1a00f2a59aef8a10e
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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