Acetic Acid → HCID 18409471, compound

HRID 993320Notes

Reaction equation

HRID 993320 reaction equation
[CH3:1][C:2]([CH3:29])([CH3:28])[C:3](=[O:27])[CH2:4][O:5][C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:9]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[NH:8][N:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:42](O)(=[O:44])[CH3:43]>C1(C)C=CC=CC=1>[C:42]([N:8]1[C:9]([C:17]2[CH:18]=[CH:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][CH:22]=2)=[C:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:6]([O:5][CH2:4][C:3](=[O:27])[C:2]([CH3:29])([CH3:28])[CH3:1])=[N:7]1)(=[O:44])[CH3:43]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 521998p-Toluenesulfonic acid monohydrateHCID 18409498HCID 18409498, compound

Product 1

HCID 18409471HCID 18409471, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3,3-dimethyl-1-[(5-(4-(methylsulphonyl)phenyl)-4-phenyl-1H-pyrazol-3-yl)oxy]butan-2-one (145 mg, 0.35 mmol), prepared according to the method of Example 32B, p-toluene-sulfonic acid hydrate (15 mg), and molecular sieves (4 g) in toluene (35 mL) and acetic acid (5 mL) was refluxed for 24 hours. The mixture was concentrated in vacuo, and the residue was purified by chromatography (silica gel, 1:1 hexanes-ethyl acetate) to provide the desired product (yield: 30 mg; 19%). MP 189-191° C.; MS (APCI+) m/z 455 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ1.22 (s, 9H), 2.48 (s, 3H), 3.28 (s, 3H), 5.37 (s, 2H), 7.23 (m, 5H), 7.60 (d, J=9 Hz, 2H), 7.90 (d, J=9 Hz, 2H); Anal. calc. for C24H26N2O5S.0.5 H2O: C, 62.18; H, 5.87; N, 6.04. Found: C, 62.38; H, 5.81; N, 5.83.

Workup

  1. customprepared
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by chromatography (silica gel, 1:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-e09776a034fa476bbc888e1c0f412dea
Source dataset
uspto-grants-2002_10
Patent number
US06472416B1

Reaction notes

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