N,N-二甲基甲酰胺 → N-(3-{[2-(acetylamino)imidazo[1,2-b]pyridazin-6-yl]oxy}phenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 2391245

反应方程式

HRID 2391245 反应方程式
[CH3:1][N:2]1[C:6]([C:7]([OH:9])=O)=[CH:5][C:4]([CH3:10])=[N:3]1.CN(C)C=O.C(Cl)(=O)C(Cl)=O.[NH2:22][C:23]1[CH:24]=[C:25]([CH:40]=[CH:41][CH:42]=1)[O:26][C:27]1[CH:28]=[CH:29][C:30]2[N:31]([CH:33]=[C:34]([NH:36][C:37](=[O:39])[CH3:38])[N:35]=2)[N:32]=1>O1CCCC1.CN(C)C(=O)C.O>[C:37]([NH:36][C:34]1[N:35]=[C:30]2[CH:29]=[CH:28][C:27]([O:26][C:25]3[CH:24]=[C:23]([NH:22][C:7]([C:6]4[N:2]([CH3:1])[N:3]=[C:4]([CH3:10])[CH:5]=4)=[O:9])[CH:42]=[CH:41][CH:40]=3)=[N:32][N:31]2[CH:33]=1)(=[O:39])[CH3:38]

参与物

8

反应物 4

HCID 6228N,N-二甲基甲酰胺HCID 65578草酰氯HCID 5877211,3-二甲基-1H-吡唑-5-甲酸HCID 57441053N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]acetamide

产物 1

HCID 57505506N-(3-{[2-(acetylamino)imidazo[1,2-b]pyridazin-6-yl]oxy}phenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide收率 67%

试剂、催化剂与溶剂 3

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8028四氢呋喃溶剂HCID 31374N,N-二甲基乙酰胺溶剂2 次

实验过程

To a solution (4.0 mL) of 1,3-dimethyl-1H-pyrazole-5-carboxylic acid (109 mg, 0.85 mmol) in tetrahydrofuran were added N,N-dimethylformamide (30 μL, 0.39 mmol) and oxalyl chloride (135 μL, 1.55 mmol), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and a solution of the residue in N,N-dimethylacetamide (2.0 mL) was added dropwise to a solution of N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]acetamide (200 mg, 0.71 mmol) in N,N-dimethylacetamide (2.0 mL). After the reaction mixture was stirred at room temperature for 1 hr, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran, washed with saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate to give the title compound (182 mg, 67%) as a white powder.

后处理

  1. customThe solvent was evaporated under reduced pressure
  2. stirringAfter the reaction mixture was stirred at room temperature for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. customThe solvent was evaporated under reduced pressure
  8. washthe residue was washed with ethyl acetate

来源与证据

ORD记录
ord-cd91b1807da24b31b86395eaff2c2c37
来源数据集
uspto-grants-2012_09
专利号
US08273741B2

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