Triethylamine → HCID 57505728, compound

HRID 1663997Notes

Reaction equation

HRID 1663997 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[N:11]=1.[C:24]([C:28]1[CH:32]=[C:31]([NH:33][C:34](=O)[O:35]CC(Cl)(Cl)Cl)[N:30]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:29]=1)([CH3:27])([CH3:26])[CH3:25].C(N(CC)CC)C>CS(C)=O.O.C(OCC)(=O)C>[C:24]([C:28]1[CH:32]=[C:31]([NH:33][C:34]([NH:1][C:2]2[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=2)[O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]4[CH2:20][CH2:19]4)=[O:17])[N:14]=3)[N:11]=2)=[O:35])[N:30]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:29]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 45926015HCID 45926015, compoundHCID 57386059N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57505728HCID 57505728, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Conditions

Temperature
85 °C

Procedure

To a solution of N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (160 mg, 0.52 mmol) and 2,2,2-trichloroethyl (3-tert-butyl-1-phenyl-1H-pyrazol-5-yl)carbamate (200 mg, 0.52 mmol) in dimethylsulfoxide/water (2.0 mL/1.5 mL) was added triethylamine (53 mg, 0.52 mmol), and the mixture was stirred at 85° C. for 8 hr. The reaction mixture was diluted with ethyl acetate, washed with 1N hydrochloric acid, 5% aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate/hexane=50/50→100/0) and precipitated from ethyl acetate/diisopropyl ether/hexane to give the title compound (285 mg, 99%) as a white powder.

Workup

  1. washwashed with 1N hydrochloric acid, 5% aqueous sodium hydrogencarbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltrated
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by NH silica gel column chromatography (ethyl acetate/hexane=50/50→100/0)
  6. customprecipitated from ethyl acetate/diisopropyl ether/hexane

Sources & evidence

ORD record
ord-2b73b3905c0a48a49c7b5765fd89c71f
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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