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

HRID 1874543노트

반응식

HRID 1874543 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0f2fab648e1b4121b9405e2d9d836f20
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304557B2

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