Dimethyl Sulfoxide → HCID 86682369, compound

HRID 2283643Notes

Reaction equation

HRID 2283643 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[C:10]([N+:20]([O-:22])=[O:21])=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][O:15]3)[CH:13]=2)[CH:3]=1.[C:23](=[O:26])([O-])[O-:24].[K+].[K+].C(OC(=O)N([S:41]([C:44]1[CH:49]=[C:48]([Cl:50])[C:47](F)=[CH:46][C:45]=1[F:52])(=[O:43])=[O:42])C1N=CSC=1)(C)(C)C.[CH3:54][S:55]([CH3:57])=O>C(OCC)(=O)C>[C:4]([O:24][C:23](=[O:26])[NH:20][C:10]1[N:11]=[C:54]([S:41]([C:44]2[CH:49]=[C:48]([Cl:50])[C:47]([O:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=3[C:9]3[C:10]([N+:20]([O-:22])=[O:21])=[N:11][N:12]([CH:14]4[CH2:19][CH2:18][CH2:17][CH2:16][O:15]4)[CH:13]=3)=[CH:46][C:45]=2[F:52])(=[O:42])=[O:43])[S:55][CH:57]=1)([CH3:9])([CH3:5])[CH3:3]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 59436581Tert-butyl (5-chloro-2,4-difluorophenyl)sulfonyl(thiazol-4-yl)carbamateHCID 666528634-Fluoro-2-[3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]phenol

Product 1

HCID 86682369HCID 86682369, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-fluoro-2-[3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]phenol (Preparation 27, 50.5 mg, 0.16 mmol) and potassium carbonate (45.4 mg, 0.33 mmol) in dimethylsulfoxide (1.0 mL) was stirred for 10 minutes at ambient temperature. tert-Butyl[(5-chloro-2,4-difluorophenyl)sulfonyl]1,3-thiazol-4-ylcarbamate (Preparation 4, 67.5 mg, 0.16 mmol) was added, and the reaction mixture was stirred at ambient temperature. After 24 hours, the reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by automated silica gel flash chromatography (10% to 100% ethyl acetate in hexanes gradient elution) to afford the title compound as a white solid (85 mg, 76%).

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature
  2. waitAfter 24 hours
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by automated silica gel flash chromatography (10% to 100% ethyl acetate in hexanes gradient elution)

Sources & evidence

ORD record
ord-e8591f3e1c57435db93ba9a888b7853b
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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