Triethylamine → HCID 86623154, compound

HRID 1360894Notes

Reaction equation

HRID 1360894 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.CC1(C)[O:33][CH:32]([CH2:34][NH2:35])[CH2:31][O:30]1>C(Cl)Cl>[Br:16][C:15]1[S:14][C:13]([S:17](=[O:19])(=[O:18])[NH:35][CH2:34][CH:32]([OH:33])[CH2:31][OH:30])=[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 41223491,3-Dioxolane-4-methanamine, 2,2-dimethyl-HCID 866231464-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonylchloride

Product 1

HCID 86623154HCID 86623154, compoundYield 94%

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 2,2-dimethyl-1,3-dioxolane-4-methanamine (0.31 ml; 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 (3650 mg; 94%).

Workup

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

Sources & evidence

ORD record
ord-546f270e12c544d0bfe8e5c2bdf5a541
Source dataset
uspto-grants-2011_02
Patent number
US07879888B2

Reaction notes

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