2,5-Dimethyl-2H-pyrazole-3-carbonyl chloride → N-[3-({2-[(N,N-dimethylglycyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 2391275

反応式

HRID 2391275 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16](=[O:21])[CH2:17][N:18]([CH3:20])[CH3:19])[N:14]=2)[N:11]=1.[CH3:25][N:26]1[C:30]([C:31](Cl)=[O:32])=[CH:29][C:28]([CH3:34])=[N:27]1>CN1CCCC1=O.[OH-].[Na+]>[CH3:19][N:18]([CH3:20])[CH2:17][C:16]([NH:15][C:13]1[N:14]=[C:9]2[CH:8]=[CH:7][C:6]([O:5][C:4]3[CH:3]=[C:2]([NH:1][C:31]([C:30]4[N:26]([CH3:25])[N:27]=[C:28]([CH3:34])[CH:29]=4)=[O:32])[CH:24]=[CH:23][CH:22]=3)=[N:11][N:10]2[CH:12]=1)=[O:21]

参加物

5

反応物 2

HCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 57708553N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]-N2,N2-dimethylglycinamide

生成物 1

HCID 24767980N-[3-({2-[(N,N-dimethylglycyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide収率 49%

試薬・触媒・溶媒 2

HCID 13387N-methyl-2-pyrrolidone溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

To a solution of N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]-N2,N2-dimethylglycinamide (196 mg, 0.6 mmol) in N-methylpyrrolidone (5.0 mL) was added 1,3-dimethylpyrazole-5-carbonyl chloride (270 mg, 1.7 mmol), and the mixture was stirred at room temperature for 5 hr. The reaction mixture was diluted with 1N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→460/40) and precipitated from ethyl acetate to give the title compound (131 mg, 49%) as a white powder. melting point 210° C.

後処理

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→460/40)
  4. customprecipitated from ethyl acetate

出典と根拠

ORDレコード
ord-bb0344d669744857a7803d339af9601e
出典データセット
uspto-grants-2012_09
特許番号
US08273741B2

関連ノート

読み込み中…