Dimethylamine → N-(5-{5-[(Dimethylamino)sulfonyl]-2-thienyl}-4-methyl-1,3-thiazol-2-YL)acetamide

HRID 1360869Notes

Reaction equation

HRID 1360869 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].[CH3:20][NH:21][CH3:22].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:20][N:21]([CH3:22])[S:16]([C:14]1[S:15][C:11]([C:7]2[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=2[CH3:10])=[CH:12][CH:13]=1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

Product 1

HCID 11998549N-(5-{5-[(Dimethylamino)sulfonyl]-2-thienyl}-4-methyl-1,3-thiazol-2-YL)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride, prepared as in Step II of Example 1 (110 mg; 0.33 mmol; 1 eq), is dissolved in DMF (10 ml). Dimethylamine (0.1 ml; 1.65 mmol; 5 eq) and DIEA (0.17 ml; 0.98 mmol; 3 eq) are added. After one hour, the solvents are 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 (18) as a yellow powder (52 mg; 46%).

Workup

  1. customthe solvents are evaporated to dryness
  2. dissolutionThe crude product is re-dissolved in DCM
  3. washwashed with NH4Cl saturated solution, water
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the solvents, crude material
  6. customis precipitated in a mixture of DCM and diethyl ether
  7. customaffording
  8. filtrationafter filtration, Compound (18) as a yellow powder (52 mg; 46%)

Sources & evidence

ORD record
ord-48db0781c39a48279b09a19840263543
Source dataset
uspto-grants-2011_02
Patent number
US07879888B2

Reaction notes

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