Sodium Bicarbonate → N-[3-({2-[(cyclopropylsulfonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-3-methylpyridine-2-carboxamide

HRID 1874543Notes

Reaction equation

HRID 1874543 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([O:10][C:11]3[CH:12]=[C:13]([NH:17][C:18]([C:20]4[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=4)=[O:19])[CH:14]=[CH:15][CH:16]=3)=[CH:6][N:5]2[CH:27]=1.C(=O)([O-])O.[Na+].[CH:33]1([S:36](Cl)(=[O:38])=[O:37])[CH2:35][CH2:34]1>O1CCCC1>[CH:33]1([S:36]([NH:1][C:2]2[N:3]=[C:4]3[CH:9]=[CH:8][C:7]([O:10][C:11]4[CH:12]=[C:13]([NH:17][C:18]([C:20]5[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=5)=[O:19])[CH:14]=[CH:15][CH:16]=4)=[CH:6][N:5]3[CH:27]=2)(=[O:38])=[O:37])[CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2760919Cyclopropanesulfonyl chlorideHCID 57749390N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide

Product 1

HCID 57749131N-[3-({2-[(cyclopropylsulfonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-3-methylpyridine-2-carboxamideYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide (150 mg, 0.417 mmol), tetrahydrofuran (10 mL) and aqueous sodium hydrogen carbonate solution (5 mL) was added cyclopropanesulfonyl chloride (348 μL, 2.48 mmol), and the mixture was stirred at room temperature for 61 hr. The reaction mixture was concentrated under reduced pressure, diluted with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (0%→70% ethyl acetate-hexane) to give the title compound (43.7 mg, 23%) as a pale-yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with aqueous sodium hydrogen carbonate solution
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (0%→70% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-0f2fab648e1b4121b9405e2d9d836f20
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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