Water → N-{6-[3-({[(1,3-dimethyl-1H-pyrazol-5-yl)amino]carbonyl}amino)-4-methylphenoxy]imidazo[1,2-b]pyridazin-2-yl}cyclopropanecarboxamide

HRID 2391352Notes

Reaction equation

HRID 2391352 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][C:4]([CH3:8])=[N:3]1.C1N=CN([C:14](N2C=NC=C2)=[O:15])C=1.[NH2:21][C:22]1[CH:23]=[C:24]([CH:41]=[CH:42][C:43]=1[CH3:44])[O:25][C:26]1[CH:27]=[CH:28][C:29]2[N:30]([CH:32]=[C:33]([NH:35][C:36]([CH:38]3[CH2:40][CH2:39]3)=[O:37])[N:34]=2)[N:31]=1.O>CN(C)C=O>[CH3:1][N:2]1[C:6]([NH:7][C:14]([NH:21][C:22]2[CH:23]=[C:24]([CH:41]=[CH:42][C:43]=2[CH3:44])[O:25][C:26]2[CH:27]=[CH:28][C:29]3[N:30]([CH:32]=[C:33]([NH:35][C:36]([CH:38]4[CH2:40][CH2:39]4)=[O:37])[N:34]=3)[N:31]=2)=[O:15])=[CH:5][C:4]([CH3:8])=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 5207211,3-Dimethyl-1H-pyrazol-5-amineHCID 57505476N-[6-(3-amino-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57505593N-{6-[3-({[(1,3-dimethyl-1H-pyrazol-5-yl)amino]carbonyl}amino)-4-methylphenoxy]imidazo[1,2-b]pyridazin-2-yl}cyclopropanecarboxamideYield 20.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,3-dimethyl-1H-pyrazol-5-amine (104 mg, 0.93 mmol) in N,N-dimethylformamide (4.0 mL) was added N,N-carbonyldiimidazole (150 mg, 0.93 mmol), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added N-[6-(3-amino-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (200 mg, 0.62 mmol), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran, washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethanol/ethyl acetate=1/20→1/10) to give the title compound (58 mg, 20%) as a white powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hr
  2. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltrated
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethanol/ethyl acetate=1/20→1/10)

Sources & evidence

ORD record
ord-4befa6cd77814422a898d73649e8559e
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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