HCID 86623153, compound → HCID 11998799, compound

HRID 1948438Notes

Reaction equation

HRID 1948438 reaction equation
Br[C:2]1[S:3][C:4]([S:17]([N:20]2[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]2)(=[O:19])=[O:18])=[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>[OH:26][CH:23]1[CH2:22][CH2:21][N:20]([S:17]([C:4]2[S:3][CH:2]=[C:6]([C:7]3[S:11][C:10]([NH:12][C:13](=[O:15])[CH3:14])=[N:9][C:8]=3[CH3:16])[CH:5]=2)(=[O:19])=[O:18])[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 86623153HCID 86623153, compoundHCID 178418339Butyllithium

Product 1

HCID 11998799HCID 11998799, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

To N-{5-[2-Bromo-5-(4-hydroxy-piperidine-1-sulfonyl)-thiophen-3-yl]-4-methyl-thiazol-2-yl}-acetamide obtained in Step I as described above (3500 mg; 6.27 mmol; 1 eq), is dissolved in anhydrous THF (150 ml). The reaction mixture is cooled down to −70° C. and put under nitrogen. n-Butyllithium (18.8 ml; 1.6 M; 37.6 mmol; 6 eq) is added dropwise. The reaction is stirred over weekend and is quenched with water. Solvents are evaporated and the resulting crude product is dissolved in EtOAc, washed with water (2 times), brine and dried over MgSO4. After evaporation of the solvents, the resulting product is suspended in ACN and filtered, affording Compound (39) as a beige solid (830 mg; 32%).

Workup

  1. customis quenched with water
  2. customSolvents are evaporated
  3. dissolutionthe resulting crude product is dissolved in EtOAc
  4. washwashed with water (2 times), brine
  5. dry with materialdried over MgSO4
  6. customAfter evaporation of the solvents
  7. filtrationfiltered

Sources & evidence

ORD record
ord-92ef51c911304978ad0fbd2861faf67f
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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