Triethylamine → HCID 86623153, compound

HRID 1948437Notes

Reaction equation

HRID 1948437 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.[OH:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>C(Cl)Cl>[Br:16][C:15]1[S:14][C:13]([S:17]([N:32]2[CH2:33][CH2:34][CH:29]([OH:28])[CH2:30][CH2:31]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 79341Piperidin-4-olHCID 866231464-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonylchloride

Product 1

HCID 86623153HCID 86623153, compoundYield 88%

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 (3000 mg; 7.22 mmol; 1 eq), is dissolved in anhydrous DCM (400 ml). The reaction is put under nitrogen. Triethylamine (5.0 ml; 36.1 mmol; 5 eq) and 4-hydroxypiperidine (3649.4 mg; 36.1 mmol; 5 eq) are added successively and the reaction mixture is stirred for 6 hours at room temperature. It is washed with water, NaHCO3 sat., brine, and dried over MgSO4, affording the title compound (3500 mg; 88%).

Workup

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

Sources & evidence

ORD record
ord-c243414b8fb346cb9b71d174e5b6565a
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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