Triethylamine → HCID 11998305, compound

HRID 1948397Notes

Reaction equation

HRID 1948397 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][N:21]([CH3:26])[CH2:22][CH2:23][NH:24][CH3:25].C(N(CC)CC)C>C(Cl)Cl>[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][N:24]([CH3:25])[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 8471TriethylamineHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

Product 1

HCID 11998305HCID 11998305, compoundYield 41%

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 (500 mg; 1.48 mmol; 1 eq), is dissolved in anhydrous DCM (50 ml). The reaction is put under nitrogen. N,N,N′-Trimethyl-ethane-1,2-diamine (0.58 ml; 5.94 mmol; 3 eq) and triethylamine (0.83 ml; 5.94 mmol; 4 eq) are added successively and the reaction mixture is stirred overnight at room temperature. The reaction mixture is washed with NH4Cl sat. (2 times), water (3 times), brine, and dried over MgSO4. After evaporation of the solvents, the crude product is suspended in ACN, filtered and dried under vacuum, affording Compound (5) as a beige solid (309 mg; 41%).

Workup

  1. washThe reaction mixture is washed with NH4Cl sat. (2 times), water (3 times), brine
  2. dry with materialdried over MgSO4
  3. customAfter evaporation of the solvents
  4. filtrationfiltered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-c94442cd5eb0488291256bda78fb61dd
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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