Triethylamine → HCID 86652446, compound

HRID 1360889Notes

Reaction equation

HRID 1360889 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.[CH:28]12[O:37][CH:32]([O:33][CH:34]1[CH2:35][OH:36])[CH2:31][NH:30][CH2:29]2>C(Cl)Cl>[Br:16][C:15]1[S:14][C:13]([S:17]([N:30]2[CH2:31][CH:32]3[O:37][CH:28]([CH:34]([CH2:35][OH:36])[O:33]3)[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

5

Reactant 3

HCID 8471TriethylamineHCID 66960353HCID 66960353, compoundHCID 866231464-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonylchloride

Product 1

HCID 86652446HCID 86652446, compoundYield 77%

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 (400 mg; 0.96 mmol; 1 eq), is dissolved in anhydrous DCM (40 ml). The reaction is put under nitrogen. Triethylamine (0.67 ml; 4.81 mmol; 3 eq) and (6,8-Dioxa-3-aza-bicyclo[3.2.1]oct-7-yl)-methanol (349.2 mg; 2.41 mmol; 2.5 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 (450 mg; 77%).

Workup

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

Sources & evidence

ORD record
ord-06a721fb83ba448a82965061b5cf9500
Source dataset
uspto-grants-2011_02
Patent number
US07879888B2

Reaction notes

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