Triethylamine → HCID 86623156, compound

HRID 1360897Notes

Reaction equation

HRID 1360897 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[CH:12]=[C:13]([S:17](Cl)(=[O:19])=[O:18])[S:14][C:15]=2[Br:16])=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[CH2:21]([N:23](CC)[CH2:24][CH3:25])[CH3:22].N1CC=CC1>C(Cl)Cl>[Br:16][C:15]1[S:14][C:13]([S:17]([N:23]2[CH2:24][CH:25]=[CH:22][CH2:21]2)(=[O:19])=[O:18])=[CH:12][C:11]=1[C:7]1[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=1[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660593-PyrrolineHCID 866231464-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonylchloride

Product 1

HCID 86623156HCID 86623156, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonyl chloride, prepared as in Step III of Example 23 (500 mg; 1.2 mmol; 1 eq), is dissolved in anhydrous DCM (30 ml). The reaction is put under nitrogen. Triethylamine (0.34 ml; 2.41 mmol; 2 eq) and 3-pyrroline (166.2 mg; 2.41 mmol; 2 eq) are added successively and the reaction mixture is stirred overnight at room temperature. It is then washed with water, NH4Cl sat., brine and dried over MgSO4, affording the title compound (600 mg; 99%).

Workup

  1. washIt is then washed with water, NH4Cl sat., brine
  2. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-d24655525bb8470cbaf9a2427180dd54
Source dataset
uspto-grants-2011_02
Patent number
US07879888B2

Reaction notes

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