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

HRID 2382864Notes

Reaction equation

HRID 2382864 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]=[CH:4][CH:3]=1.[CH:20]1([SH:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C1COCC1>[CH:20]1([S:26][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)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 15290CyclohexanethiolHCID 25212516N-(5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide

Product 1

HCID 25214735N-[5-(cyclohexylthio)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamideYield 44.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide ((B4), 136 mg; 0.5 mmol; 1.0 eq.) in dry THF (10 mL) was added in one pot cyclohexyl mercaptan (58 mg; 0.5 mmol; 1.0 eq.). The reaction mixture was stirred at rt for 14 h. The product precipitated upon addition of water after which filtration and washing with MeOH and Et2O gave the title compound as a white solid (78 mg, 44%). HPLC, Rt: 2.94 min. (purity 94.6%). LC/MS, M+(ESI): 354.1, M−(ESI): 352.0.

Workup

  1. customThe product precipitated upon addition of water
  2. filtrationafter which filtration
  3. washwashing with MeOH and Et2O

Sources & evidence

ORD record
ord-6e330b3915df410cba22e131ac06e403
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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