Dimethylformamide → HCID 86761269, compound

HRID 1360883Notes

Reaction equation

HRID 1360883 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].C(N(CC)CC)C.[NH:28]1[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29]1.CN(C=O)C>C(Cl)Cl>[Br:16][C:15]1[S:14][C:13]([S:17]([N:28]2[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29]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

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 982104-HydroxypyrrolidineHCID 866231464-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonylchloride

Product 1

HCID 86761269HCID 86761269, compoundYield 83%

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 (300 mg; 0.72 mmol; 1 eq), is dissolved in anhydrous DCM (20 ml). The solution is put under nitrogen. Triethylamine (0.5 ml; 3.61 mmol; 5 eq) and 3-pyrrolidinol (0.3 ml; 3.61 mmol; 5 eq) are added successively. DMF (0.2 ml) is added and the reaction mixture is stirred for 1 hour at room temperature. It is then washed with water, NaHCO3 sat., brine and dried over MgSO4, affording the title compound (310 mg; 83%).

Workup

  1. washIt is then washed with water, NaHCO3 sat., brine
  2. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-4ccb85487f86486fba6d38d7db57a8e8
Source dataset
uspto-grants-2011_02
Patent number
US07879888B2

Reaction notes

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