2,6-Lutidine → HCID 178477544, compound

HRID 1931541Notes

Reaction equation

HRID 1931541 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]([NH2:8])=[O:7])=[N:2]1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25])(=O)=O>ClCCCl.ClCCl>[CH2:24]([Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[NH:8][C:6]([C:3]1[N:4]=[CH:5][NH:1][N:2]=1)=[O:7])[CH3:25]

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 178513825HCID 178513825, compound

Product 1

HCID 178477544HCID 178477544, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A stirred mixture of 1H-1,2,4-triazole-3-carboxamide (500 mg, 4.46 mmol) in 1,2-dichloroethane (4.46 mL) treated at room temperature with 2,6-lutidine (2.08 mL, 17.84 mmol) and triethylsilyl trifluoromethanesulfonate (3.03 mL, 13.38 mmol) and heated under a nitrogen atmosphere at 50° C. After 4 hours of heating the reaction solution allowed to cool to room temperature and diluted with dichloromethane (25 mL), washed with water (25 mL), 0.5M hydrochloric acid (25 mL), water (25 mL), dried over MgSO4, filtered, and evaporated to solid. The solid was flash chromatographed (silica gel, 10-65% ethyl acetate:hexane) to give the product as a white solid (683 mg).

Workup

  1. temperatureAfter 4 hours of heating the reaction solution
  2. temperatureto cool to room temperature
  3. washwashed with water (25 mL), 0.5M hydrochloric acid (25 mL), water (25 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to solid
  7. customchromatographed (silica gel, 10-65% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-b59cfd08d5804f0db8f61d58a53ad391
Source dataset
uspto-grants-2012_05
Patent number
US08188085B2

Reaction notes

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