Triethylamine → HCID 86710128, compound

HRID 1468300Notes

Reaction equation

HRID 1468300 reaction equation
[Cl:1][C:2]1[C:3]([C:18]#[N:19])=[CH:4][C:5]2[N:6]([C:8]([S:14](O)(=[O:16])=[O:15])=[C:9]([CH:11]([CH3:13])[CH3:12])[N:10]=2)[CH:7]=1.C(N(CC)CC)C.P(Cl)(Cl)([Cl:29])=O>ClC(Cl)C>[Cl:1][C:2]1[C:3]([C:18]#[N:19])=[CH:4][C:5]2[N:6]([C:8]([S:14]([Cl:29])(=[O:16])=[O:15])=[C:9]([CH:11]([CH3:13])[CH3:12])[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 86710129HCID 86710129, compound

Product 1

HCID 86710128HCID 86710128, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

6-Chloro-7-cyano-2-isopropylimidazo[1,2-a]pyridine-3-sulfonic acid (2.16 g, 7.21 mmol) obtained in step 2 was dissolved in dichloroethane (20 mL), and the solution was stirred at 100° C. for 4 hours after adding triethylamine (2.01 mL, 14.4 mmol) and phosphorus oxychloride (1.34 mL, 14.4 mL). The reaction mixture was extracted with chloroform after adding water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→80/20) to give 6-chloro-7-cyano-2-isopropylimidazo[1,2-a]pyridine-3-sulfonylchloride (1.73 g, yield 75%).

Workup

  1. extractionThe reaction mixture was extracted with chloroform
  2. additionafter adding water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was then evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→80/20)

Sources & evidence

ORD record
ord-f6a16ba424e54464a659852c405ab8db
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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