HCID 86623152, compound → HCID 11998796, compound

HRID 1948432Notes

Reaction equation

HRID 1948432 reaction equation
Br[C:2]1[S:3][C:4]([S:17](=[O:26])(=[O:25])[N:18]([CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[CH3:19])=[CH:5][C:6]=1[C:7]1[S:11][C:10]([NH:12][C:13](=[O:15])[CH3:14])=[N:9][C:8]=1[CH3:16].C([Li])CCC>C1COCC1>[CH3:24][N:22]([CH3:23])[CH2:21][CH2:20][N:18]([CH3:19])[S:17]([C:4]1[S:3][CH:2]=[C:6]([C:7]2[S:11][C:10]([NH:12][C:13](=[O:15])[CH3:14])=[N:9][C:8]=2[CH3:16])[CH:5]=1)(=[O:25])=[O:26]

Participants

4

Reactant 2

HCID 86623152HCID 86623152, compoundHCID 178418339Butyllithium

Product 1

HCID 11998796HCID 11998796, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

N-(5-{2-Bromo-5-[(2-dimethylamino-ethyl)-methyl-sulfamoyl]-thiophen-3-yl}-4-methyl-thiazol-2-yl)-acetamide obtained in Step I as described above (750 mg; 1.56 mmol; 1 eq), is dissolved in anhydrous THF (60 ml). The reaction mixture is cooled down to −70° C. and put under nitrogen. n-Butyllithium (6.2 ml; 1.6 M; 12.5 mmol; 8 eq) is added dropwise. The reaction is stirred 1 hour and is quenched with water. Solvents are evaporated and the resulting residue is dissolved in EtOAc, washed with water (2 times), brine and dried over MgSO4. After evaporation of the solvent, the resulting product is suspended in a mixture of ether-DCM and filtered, affording Compound (36) as a brown solid (582 mg; 87%).

Workup

  1. customis quenched with water
  2. customSolvents are evaporated
  3. dissolutionthe resulting residue is dissolved in EtOAc
  4. washwashed with water (2 times), brine
  5. dry with materialdried over MgSO4
  6. customAfter evaporation of the solvent
  7. additionthe resulting product is suspended in a mixture of ether-DCM
  8. filtrationfiltered

Sources & evidence

ORD record
ord-1d9fe42154cb4aedb0c6dff751c27197
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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