Triethylamine → HCID 86652441, compound

HRID 1948417Notes

Reaction equation

HRID 1948417 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.[N:28]1([CH2:34][CH2:35][NH2:36])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>C(Cl)Cl>[Br:16][C:15]1[S:14][C:13]([S:17](=[O:19])(=[O:18])[NH:36][CH2:35][CH2:34][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[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 4082852-MorpholinoethylamineHCID 866231464-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]-5-bromothiophene-2-sulfonylchloride

Product 1

HCID 86652441HCID 86652441, compoundYield 14%

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, (586 mg; 1.41 mmol; 1 eq) is dissolved in anhydrous DCM (15 ml). The reaction is put under nitrogen. Then triethylamine (1.96 ml; 14.1 mmol; 10 eq) and 2-morpholin-4-yl-ethylamine (367 mg; 2.82 mmol; 2 eq) are added successively and the reaction mixture is stirred at room temperature for 30 minutes. Solvents are evaporated and the resulting crude product is purified by preparative HPLC, affording the title compound (100 mg; 14%).

Workup

  1. customSolvents are evaporated
  2. customthe resulting crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-820d9ab62f244c87876474cc80055ece
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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