Triethylamine → HCID 67000954, compound

HRID 268975Notes

Reaction equation

HRID 268975 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([CH3:10])[CH:4]=1.[Br:11][C:12]1[S:16][C:15]([S:17](Cl)(=[O:19])=[O:18])=[CH:14][CH:13]=1.C(N(CC)CC)C>C1COCC1>[CH3:10][C:5]1[CH:4]=[C:3]([CH2:2][NH:1][S:17]([C:15]2[S:16][C:12]([Br:11])=[CH:13][CH:14]=2)(=[O:19])=[O:18])[CH:8]=[C:7]([CH3:9])[N:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27339245-Bromothiophene-2-sulfonyl chlorideHCID 135828191-(2,6-Dimethylpyridin-4-yl)methanamine

Product 1

HCID 67000954HCID 67000954, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of commercially available 4-aminomethyl-2,6-dimethyl-pyridine [CAS-No. 324571-98-4] (0.24 g, 1.76 mmol) in THF (8 ml) was added at 0° C. (ice water bath) commercially available 5-bromo-thiophene-2-sulfonyl chloride (0.46 g, 1.76 mmol) dissolved in THF (8 ml) and triethylamine (0.27 ml, 1.94 mmol). The reaction mixture was stirred at room temperature for 16 h and evaporated. The crude product was further purified by flash chromatography (ethyl acetate/heptane) and crystallization from dichloromethane/hexane to yield the title compound (0.33 g, 52%) as a light red solid. MS (ISN) 359.0 [(M−H)−], mp 138° C.

Workup

  1. customevaporated
  2. customThe crude product was further purified by flash chromatography (ethyl acetate/heptane) and crystallization from dichloromethane/hexane

Sources & evidence

ORD record
ord-5c7081e20f90439bbd6e3bbf8e6df6c4
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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