Methanol → N-(4-Benzoylpyrrolidino)-1-(4-methoxyphenyl)-3-(methylsulfonyl)-1H-pyrazole-5-carboxamide

HRID 394790Notes

Reaction equation

HRID 394790 reaction equation
[C:1]([CH:9]1[CH2:13][N:12]([NH:14][C:15]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:20]=[C:19](SC)[CH:18]=2)=[O:16])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[O:33][S:34]([O-:36])=O.[K+].[CH3:38]O>O>[C:1]([CH:9]1[CH2:13][N:12]([NH:14][C:15]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:20]=[C:19]([S:34]([CH3:38])(=[O:36])=[O:33])[CH:18]=2)=[O:16])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10238249N-(4-benzoylpyrrolidino)-1-(4-methoxyphenyl)-3-(methylthio)-1H-pyrazole-5-carboxamideHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 10174009N-(4-Benzoylpyrrolidino)-1-(4-methoxyphenyl)-3-(methylsulfonyl)-1H-pyrazole-5-carboxamideYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

N-(4-benzoylpyrrolidino)-1-(4-methoxyphenyl)-3-(methylthio)-1H-pyrazole-5-carboxamide (200 mg, 0.46 mmol) was dissolved in MeOH (6 mL). A solution of Oxone (561 mg, 0.91 mmol) in H2O (3 mL) was added, and the resulting mixture stirred at room temperature under Ar for 17 hours. The reaction was diluted with H2O and extracted twice with CHCl3. The combined organic extracts were dried over Na2SO4, filtered, and evaporated. The crude product was purified by preparative HPLC on a C-18 reversed-phase column (10-70% MeCN/H2O/0.05% TFA) to yield a white powder (200 mg, 93%). 1H NMR (CDCl3): δ 8.98 (s, 1H), 7.52 (s, 1H), 7.39 (m, 6H), 6.95 (d, 2H, J=8.8), 3.84 (s, 3H), 3.65 (t, 2H, J=6.6), 3.41 (t, 2H, J=6.2), 3.28 (s, 3H), 1.93 (m, 4H).

Workup

  1. extractionextracted twice with CHCl3
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by preparative HPLC on a C-18 reversed-phase column (10-70% MeCN/H2O/0.05% TFA)

Sources & evidence

ORD record
ord-d9b8f86e8d6b40dd8ad9d576e79d2b51
Source dataset
uspto-grants-2003_08
Patent number
US06602895B2

Reaction notes

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