N,N'-Dimethylethylenediamine → HCID 11998550, compound

HRID 1948409Notes

Reaction equation

HRID 1948409 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(CC)CC)C.[CH3:27][NH:28][CH2:29][CH2:30][NH:31][CH3:32]>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:28]([CH3:27])[CH2:29][CH2:30][NH:31][CH3:32])(=[O:18])=[O:17])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 8471TriethylamineHCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

Product 1

HCID 11998550HCID 11998550, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride, prepared as in Step II of Example 1 (500 mg; 1.48 mmol; 1.00 eq), is dissolved in DCM (30 ml). The solution is degassed with N2 and cooled down to 0° C. Triethylamine (1 ml; 7.42 mmol; 5.00 eq) followed by N,N′-dimethylethylenediamine (0.79 ml; 7.42 mmol; 5.00 eq) are added. After 30 minutes at 0° C., the reaction is complete. The reaction mixture is washed with NaHCO3 sat. (twice) and water (twice). The organic phase is dried over MgSO4, filtered and concentrated under vacuum, affording Compound (19) as a beige solid (457 mg; 79%).

Workup

  1. customThe solution is degassed with N2
  2. additionare added
  3. washThe reaction mixture is washed with NaHCO3 sat. (twice) and water (twice)
  4. dry with materialThe organic phase is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-65647c06cff14eef98e94a3fd21aee7f
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

Loading…