Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → {5-tert-Butyl-2-[3-(2-hydroxy-ethoxy)-phenyl]-2H-pyrazol-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 2282711Notes

Reaction equation

HRID 2282711 reaction equation
[Cl:1][C:2]([Cl:34])([Cl:33])[CH2:3][O:4][C:5](=[O:32])[NH:6][C:7]1[N:8]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][O:25]C3CCCCO3)[CH:17]=2)[N:9]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[Cl:33][C:2]([Cl:1])([Cl:34])[CH2:3][O:4][C:5](=[O:32])[NH:6][C:7]1[N:8]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][OH:25])[CH:17]=2)[N:9]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86686679(5-tert-Butyl-2-{3-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester

Product 1

HCID 59151941{5-tert-Butyl-2-[3-(2-hydroxy-ethoxy)-phenyl]-2H-pyrazol-3-yl}-carbamic acid 2,2,2-trichloro-ethyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A colourless solution of Intermediate 39b (120 mg, 0.224 mmol) and pyridinium p-toluenesulfonate (169 mg, 0.673 mmol) in MeOH (5 mL) was stirred at 40° C. for 90 min. The solution was concentrated in vacuo, suspended in water (3 mL) and sat. aq. NaHCO3 solution (3 mL), then extracted with DCM (2×5 mL). The combined organics were passed through a hydrophobic frit, concentrated in vacuo and azeotroped with toluene (2×5 mL) to leave the title compound as a white solid (100 mg, 99%). LCMS (Method 3): Rt 4.01 min, m/z 450, 452 [MH+].

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. extractionsat. aq. NaHCO3 solution (3 mL), then extracted with DCM (2×5 mL)
  3. concentrationconcentrated in vacuo
  4. customazeotroped with toluene (2×5 mL)

Sources & evidence

ORD record
ord-6433c7a80d1e4844ba683e5baf0f4791
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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