Oxalyl chloride → N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-6-methylpyridine-2-carboxamide

HRID 1874389

반응식

HRID 1874389 반응식
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH2:17][C:18]1[CH:19]=[C:20]([CH:29]=[CH:30][CH:31]=1)[O:21][C:22]1[CH:23]=[CH:24][C:25]([NH2:28])=[N:26][CH:27]=1>O1CCCC1.CN(C)C=O.CN(C)C(=O)C.C(=O)([O-])O.[Na+]>[NH2:28][C:25]1[N:26]=[CH:27][C:22]([O:21][C:20]2[CH:19]=[C:18]([NH:17][C:8]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)=[O:10])[CH:31]=[CH:30][CH:29]=2)=[CH:23][CH:24]=1

참가 물질

8

반응물 3

HCID 65578Oxalyl chlorideHCID 702826-Methylpyridine-2-carboxylic acidHCID 577491665-(3-Aminophenoxy)pyridin-2-amine

생성물 1

HCID 57749288N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-6-methylpyridine-2-carboxamide수율 83%

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 8028Tetrahydrofuran용매HCID 31374Dimethylacetamide용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of 6-methylpyridine-2-carboxylic acid (5.66 g, 41.3 mmol) in tetrahydrofuran (300 mL) were added N,N-dimethylformamide (5 drops) and oxalyl chloride (7.20 mL, 83.0 mmol) at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in N,N-dimethylacetamide (200 mL). A solution of 5-(3-aminophenoxy)pyridin-2-amine (7.90 g, 39.3 mmol) in N,N-dimethylacetamide (20 mL) was added with stirring at room temperature, and the mixture was stirred at room temperature for 65 hr. The reaction mixture was diluted with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was washed with ethyl acetate-hexane to give the title compound (10.4 g, 83%) as a pale-brown solid.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in N,N-dimethylacetamide (200 mL)
  3. stirringwith stirring at room temperature
  4. stirringthe mixture was stirred at room temperature for 65 hr
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltrated
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. washthe residue was washed with ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-67706247f21840f089b392de08d9bc9e
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304557B2

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