Water → HCID 11999019, compound

HRID 1948448Notes

Reaction equation

HRID 1948448 reaction equation
Br[C:2]1[S:3][C:4]([S:17]([N:20]2[CH2:25][CH2:24][CH2:23][CH:22]([OH:26])[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.O>C1COCC1>[OH:26][CH:22]1[CH2:23][CH2:24][CH2:25][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])[CH2:21]1

Participants

5

Reactant 3

HCID 962WaterHCID 86623159HCID 86623159, compoundHCID 178418339Butyllithium

Product 1

HCID 11999019HCID 11999019, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

N-(5-{2-bromo-5-[(3-hydroxypiperidin-1-yl)sulfonyl]-3-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide obtained in Step I as described above (54 mg; 0.112 mmol; 1 eq), is dissolved in dry THF (5 ml) at −70° C. under an inert atmosphere. n-Butyllithium (0.15 ml; 1.6 M; 0.24 mmol; 2.20 eq) is added slowly and reaction stirred at −70° C. for 1 hour before being hydrolyzed with water (0.3 ml). Reaction is warmed up to room temperature before being concentrated to dryness. Residue is taken up with water (2 ml) and EtOAc (10 ml). The organic phases are decanted, dried over MgSO4, filtrated and evaporated. Title compound is purified by reverse preparative HPLC, affording expected Compound (48) as a white solid (20 mg; 43%).

Workup

  1. customreaction
  2. customReaction
  3. temperatureis warmed up to room temperature
  4. concentrationbefore being concentrated to dryness
  5. customThe organic phases are decanted
  6. dry with materialdried over MgSO4
  7. filtrationfiltrated
  8. customevaporated
  9. customTitle compound is purified by reverse preparative HPLC

Sources & evidence

ORD record
ord-cd6a938d19d7483b929a7a51b1c5df35
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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