HCID 86623152, compound → HCID 11998796, compound

HRID 1360888Notes

Reaction equation

HRID 1360888 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-85d8118bbd554cc685e2fdab99102826
Source dataset
uspto-grants-2011_02
Patent number
US07879888B2

Reaction notes

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