Trifluoromethanesulfonic anhydride → 5-Methyl-1-(4-methylbenzyl)-1H-pyrazole-3-carbonitrile

HRID 2400565Notes

Reaction equation

HRID 2400565 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]([NH2:17])=O)[CH:3]=1.C(N(CC)C(C)C)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]#[N:17])[CH:3]=1

Participants

5

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 595047015-Methyl-1-(4-methylbenzyl)-1H-pyrazole-3-carboxamide

Product 1

HCID 595046725-Methyl-1-(4-methylbenzyl)-1H-pyrazole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mechanically stirred solution of 5-methyl-1-(4-methylbenzyl)-1H-pyrazole-3-carboxamide (Step 1, 200 mg, 0.872 mmol) and N,N-diisopropylethylamine (760 μL, 4.36 mmol) in dichloromethane (10 mL) was added dropwise trifluoromethanesulfonic acid anhydride (266 μL, 1.57 mmol) at 0° C. After stirring for 30 minutes at this temperature, all volatiles were removed in vacuo. Then, in a first purification step, the crude product was subjected to preparative HPLC, followed by a second purification using MPLC (silica, dichloromethane) to afford the title compound in pure form (140 mg, 76%): 1H NMR (400 MHz, CDCl3) δ 7.13 (d, 2H), 7.02 (d, 2H), 6.43 (s, 1H), 5.27 (s, 2H), 2.33 (s, 3H), 2.21 (s, 3H); ES-MS m/z 211 (M)+; HPLC RT (Method J) 4.54 min.

Workup

  1. customall volatiles were removed in vacuo
  2. customThen, in a first purification step
  3. customfollowed by a second purification

Sources & evidence

ORD record
ord-3a341f9868544900b84ac06c84a259ad
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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