Triethylamine → HCID 11998305, compound

HRID 1360859Notes

Reaction equation

HRID 1360859 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-ab0aa50d6c5c490d84e22b96cb1623c5
Source dataset
uspto-grants-2011_02
Patent number
US07879888B2

Reaction notes

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