Water → N-(4-Methyl-5-{5-[(piperazin-1-YL)sulfonyl]-2-thienyl}-1,3-thiazol-2-YL)acetamide

HRID 1948402Notes

Reaction equation

HRID 1948402 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].C[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.CCN(C(C)C)C(C)C.O>C(Cl)Cl>[CH3:10][C:8]1[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=1[C:11]1[S:15][C:14]([S:16]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)(=[O:18])=[O:17])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

Product 1

HCID 11998431N-(4-Methyl-5-{5-[(piperazin-1-YL)sulfonyl]-2-thienyl}-1,3-thiazol-2-YL)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride, prepared as in Step II of Example 1 (280 mg; 0.84 mmol; 1 eq), is dissolved in DCM (10 ml). N-Methyl piperazine (1.4 g; 16.8 mmol; 20 eq) and DIEA (0.17 ml; 0.98 mmol; 3 eq) are added. After one night reaction, water (1 ml) is added and the solvents evaporated to dryness. The crude product is re-dissolved in DCM and washed with NH4Cl saturated solution, water and dried over MgSO4. After evaporation of the solvents, crude material is precipitated in a mixture of DCM and diethyl ether, affording after filtration, Compound (11) as a white solid (125 mg; 40%).

Workup

  1. additionis added
  2. customthe solvents evaporated to dryness
  3. dissolutionThe crude product is re-dissolved in DCM
  4. washwashed with NH4Cl saturated solution, water
  5. dry with materialdried over MgSO4
  6. customAfter evaporation of the solvents, crude material
  7. customis precipitated in a mixture of DCM and diethyl ether
  8. customaffording
  9. filtrationafter filtration, Compound (11) as a white solid (125 mg; 40%)

Sources & evidence

ORD record
ord-9a305f7c270245319f76571878e2e120
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

Loading…