Diisopropylethylamine → HCID 86615004, compound

HRID 732422Notes

Reaction equation

HRID 732422 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])[N:7]=[C:6](Cl)[CH:5]=1.C(N(CC)C(C)C)(C)C.[CH2:27]([NH2:30])[C:28]#[CH:29]>C1COCC1>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:5]=[C:6]([NH:30][CH2:27][C:28]#[CH:29])[N:7]=[C:8]([S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])[CH:9]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 239041PropargylamineHCID 86615003HCID 86615003, compound

Product 1

HCID 86615004HCID 86615004, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add THF (10 mL), 2-chloro-6-iso-propanesulfonyl-isonicotinic acid methyl ester (0.50 g, 1.80 mmol), N,N-diisopropylethylamine (0.470 mL, 2.70 mmol), and propargylamine (0.740 mL, 10.8 mmol) to a sealed vessel flushed with nitrogen. Heat and stir the reaction at 80° C. overnight. Cool to room temperature, concentrate and purify (silica gel chromatography, eluting with 20:80 to 30:70 ethyl acetate:hexanes) to give the title product (0.102 g, 19%).

Workup

  1. customflushed with nitrogen
  2. temperatureHeat
  3. customthe reaction at 80° C. overnight
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 20:80 to 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-69a9df2110b448b0aa5afce2cac2c5a8
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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