Reaction #308558

ord-1c2e781c83cf4ed4b6fd1df814147632

Reaction equation

CCCCCC1CCC(C(=O)NNC(=O)c2ccncc2)CC1
4-pentyl-cyclohexanecarboxylic acid N′-(pyridine-4-carbonyl)hydrazide
COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1
Lawesson's reagent
→
CCCCC[C@H]1CC[C@H](c2nnc(-c3ccncc3)s2)CC1
title compound
CCCCC[C@H]1CC[C@H](c2nnc(-c3ccncc3)s2)CC1
trans-4-[5-(4-Pentyl-cyclohexyl)-[1,3,4]thiadiazol-2-yl]pyridine

Reactants

CCCCCC1CCC(C(=O)NNC(=O)c2ccncc2)CC1
4-pentyl-cyclohexanecarboxylic acid N′-(pyridine-4-carbonyl)hydrazide
COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1
Lawesson's reagent

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureunder reflux for 18 h
  2. 2
    OtherThe solvent was evaporated
  3. 3
    Otherthe residue purified by flash chromatography (IH-EtOAc, 4:1

Procedure

A solution of 4-pentyl-cyclohexanecarboxylic acid N′-(pyridine-4-carbonyl)hydrazide (Preparation 19, 50 mg, 0.158 mmol) and Lawesson's reagent (127 mg, 0.32 mmol) in toluene (2 ml) was heated under reflux for 18 h. The solvent was evaporated and the residue purified by flash chromatography (IH-EtOAc, 4:1 then EtOAc) to afford the title compound: RT=5.02 min; m/z (ES+)=316.0 [M+H]+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08207147B2uspto-grants-2012_06