HCID 17838654, compound → HCID 25175693, compound

HRID 533351Notes

Reaction equation

HRID 533351 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1)(=[O:9])=[O:8].[C:20]1([Mg]Br)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[C:20]1([S:16]([C:13]2[CH:14]=[CH:15][C:10]([S:7]([NH:6][C:2]3[S:1][CH:5]=[CH:4][N:3]=3)(=[O:9])=[O:8])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 17838654HCID 17838654, compoundHCID 178418255HCID 178418255, compound2×

Product 1

HCID 25175693HCID 25175693, compoundYield 4.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

4-(N-thiazol-2-ylsulfamoyl)benzene-1-sulfonyl chloride (0.339 g, 0.00100 mol) was mixed in tetrahydrofuran (15 mL) and cooled to −78° C. Phenylmagnesium bromide (0.363 g, 0.002 mol) solution in THF (1M) was added to the reaction in a dropwise manner. The reaction was allowed to stir 1 hour while warming to room temperature. A second portion of phenyl magnesium bromide solution (0.181 g, 0.001 mol) was added to the reaction mixture. The reaction mixture was then stirred for 18 hours then quenched with saturated ammonium chloride solution. The organic phase was separated and dried over magnesium sulfate. The organic phase was evaporated to a residue and purified by column chromatography (12 g silica gel ISCO column, hexanes to ethyl acetate gradient elution). Product fractions were combined and rotary evaporated to give 15.7 mg of product as white crystals. LCMS: Rt=1.30 min, MS m/z 380.6 [MH]+.

Workup

  1. temperaturewhile warming to room temperature
  2. stirringThe reaction mixture was then stirred for 18 hours
  3. customthen quenched with saturated ammonium chloride solution
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customThe organic phase was evaporated to a residue
  7. custompurified by column chromatography (12 g silica gel ISCO column, hexanes to ethyl acetate gradient elution)
  8. customrotary evaporated

Sources & evidence

ORD record
ord-8693bd026d814338bc5ab7d5a88d23a0
Source dataset
uspto-grants-2014_10
Patent number
US08853250B2

Reaction notes

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