Triethylamine → 4-{5-[1-(4-chlorophenyl)cyclopropyl]-4-methyl-4H-1,2,4-triazol-3-yl}cyclohexanol
Reaction equation
FC(F)(F)S(OC)(=O)=O.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2([C:20]([NH:22][CH3:23])=O)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.C(N(CC)CC)C.[OH:31][CH:32]1[CH2:37][CH2:36][CH:35]([C:38]([NH:40][NH2:41])=O)[CH2:34][CH2:33]1>C1(C)C=CC=CC=1>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2([C:20]3[N:22]([CH3:23])[C:38]([CH:35]4[CH2:36][CH2:37][CH:32]([OH:31])[CH2:33][CH2:34]4)=[N:40][N:41]=3)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Methyl trifluoromethanesulfonate (53.9 μL, 0.491 mmol) was added to 1-(4-chlorophenyl)-N-methylcyclopropanecarboxamide (100.0 mg, 0.48 mmol). The resulting reaction mixture was stirred at 60° C. for 30 min. To the reaction mixture were then added toluene (2.0 mL), triethylamine (68.6 μL, 0.492 mmol) and 4-hydroxycyclohexanecarbo-hydrazide (38 mg, 0.24 mmol). The resulting mixture was stirred for 3 h at 60° C. and an additional 1 h. at 110° C. The mixture was then cooled to room temperature (about 25° C.). After cooling, the reaction mixture was concentrated to provide a residue. The residue was purified by Prep-HPLC to afford the desired products (cis- and trans-two isomers). Isomer I: LCMS: (M+H)+=332.2/334.2; isomer II: LCMS: (M+H)+=332.1/334.1.
Workup
- customThe resulting reaction mixture
- stirringThe resulting mixture was stirred for 3 h at 60° C. and an additional 1 h. at 110° C
- temperatureThe mixture was then cooled to room temperature (about 25° C.)
- temperatureAfter cooling
- concentrationthe reaction mixture was concentrated
- customto provide a residue
- customThe residue was purified by Prep-HPLC
Sources & evidence
- ORD record
- ord-ac37fa088c7b4c83a693e2328f142ff4
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07838544B2
Reaction notes
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