Triethylamine → HCID 89955016, compound

HRID 1468301Notes

Reaction equation

HRID 1468301 reaction equation
[Cl:1][C:2]1[C:3]([C:18]#[N:19])=[CH:4][C:5]2[N:6]([C:8]([S:14](Cl)(=[O:16])=[O:15])=[C:9]([CH:11]([CH3:13])[CH3:12])[N:10]=2)[CH:7]=1.Cl.[F:21][C:22]1([F:26])[CH2:25][NH:24][CH2:23]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(#N)C>[Cl:1][C:2]1[C:3]([C:18]#[N:19])=[CH:4][C:5]2[N:6]([C:8]([S:14]([N:24]3[CH2:25][C:22]([F:26])([F:21])[CH2:23]3)(=[O:16])=[O:15])=[C:9]([CH:11]([CH3:13])[CH3:12])[N:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 86710128HCID 86710128, compound

Product 1

HCID 89955016HCID 89955016, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Chloro-7-cyano-2-isopropylimidazo[1,2-a]pyridine-3-sulfonylchloride (1.00 g, 3.14 mmol) obtained in step 3 was dissolved in acetonitrile (10 mL), and the solution was stirred at room temperature for 1.25 hours after adding 3,3-difluoroazetidinehydrochloride (611 mg, 4.71 mmol) and triethylamine (1.31 mL, 9.43 mmol). A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture. The precipitated crystals were collected by filteration, and washed with water. The resulting crude product was purified by silica gel column chromatography (heptane/ethyl acetate=80/20→50/50) to give 6-chloro-3-(3,3-difluoroazetidin-1-ylsulfonyl)-2-isopropylimidazo[1,2-a]pyridine-7-carbonitrile (1.10 g, yield 93%).

Workup

  1. customThe precipitated crystals were collected by filteration
  2. washwashed with water
  3. customThe resulting crude product was purified by silica gel column chromatography (heptane/ethyl acetate=80/20→50/50)

Sources & evidence

ORD record
ord-72ae0950cf95483eb1fefe370b101c30
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

Loading…