Pyrazole → HCID 67133186, compound

HRID 659677Notes

Reaction equation

HRID 659677 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:13]=[C:12]([CH2:14][CH:15]([CH3:17])[CH3:16])[S:11][C:10]=2[S:18]([NH:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])=[O:19])[CH:6]=[CH:7][CH:8]=1.[NH:26]1[CH:30]=[CH:29][CH:28]=[N:27]1>O1CCOCC1>[N:26]1([CH2:2][C:3]2[CH:4]=[C:5]([C:9]3[CH:13]=[C:12]([CH2:14][CH:15]([CH3:17])[CH3:16])[S:11][C:10]=3[S:18]([NH:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])=[O:19])[CH:6]=[CH:7][CH:8]=2)[CH:30]=[CH:29][CH:28]=[N:27]1

Participants

4

Reactant 2

HCID 1048Pyrazole2×HCID 670039813-(3-Bromomethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

Product 1

HCID 67133186HCID 67133186, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(3-bromomethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide (90.4 mg, 0.203 mmol; see Example 1(e)) in dioxane (2.0 mL) was added pyrazole (41.5 mg, 0.609 mmol) and the reaction mixture was stirred for 18 h at 80° C., after which another portion of pyrazole (60.4 mg, 0.887 mmol) was added and the reaction mixture stirred for a further 3 h. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography using EtOAc:petroleum ether (2:8) as eluent to give the sub-title compound in 98% yield as a colourless syrup (86 mg, 0.199 mmol).

Workup

  1. stirringthe reaction mixture stirred for a further 3 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-5117669d16524cc7a72cad718a294130
Source dataset
uspto-grants-2011_12
Patent number
US08080571B2

Reaction notes

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