Triethylamine → HCID 86652446, compound

HRID 1948433Notes

Reaction equation

HRID 1948433 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-e7fc7d5327634b20aca2cccba82d5524
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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