Cyclohexylamine → N5-cyclohexyl[1,2,4]triazolo[1,5-a]pyridine-2,5-diamine

HRID 2382766Notes

Reaction equation

HRID 2382766 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH:12]1([NH2:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>CC(OC)(C)C>[CH:12]1([NH:18][C:2]2[N:7]3[N:8]=[C:9]([NH2:11])[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 214644135-Chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 25216186N5-cyclohexyl[1,2,4]triazolo[1,5-a]pyridine-2,5-diamineYield 59%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A suspension of 5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-amine ((A4), 10.0 g; 59.32 mmol; 1.0 eq.) in cyclohexylamine (60 mL) was heated to reflux for 52 h. Reaction mixture was taken up in MTBE and filtered. The resulting cake was washed with MTBE and filtrate was concentrated to dryness. Residue was purified by flash chromatography (Hept/EtOAc, 1:1) to give the title compound as a beige powder (8.08 g, 59%). HPLC, Rt: 2.46 min. (purity 98.9%). LC/MS, M+(ESI): 231.9.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 52 h
  3. customReaction mixture
  4. filtrationfiltered
  5. washThe resulting cake was washed with MTBE and filtrate
  6. concentrationwas concentrated to dryness
  7. customResidue was purified by flash chromatography (Hept/EtOAc, 1:1)

Sources & evidence

ORD record
ord-34a3cb85714541479a0e026553f350d1
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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