4-Methylmorpholine → N-(6-{3-[(3-phenylprop-2-ynoyl)amino]phenoxy}imidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

HRID 1668234Notes

Reaction equation

HRID 1668234 reaction equation
[C:1]1([C:7]#[C:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)OCC(C)C.CN1CCOCC1.[NH2:27][C:28]1[CH:29]=[C:30]([CH:47]=[CH:48][CH:49]=1)[O:31][C:32]1[CH:33]=[CH:34][C:35]2[N:36]([CH:38]=[C:39]([NH:41][C:42]([CH:44]3[CH2:46][CH2:45]3)=[O:43])[N:40]=2)[N:37]=1>O1CCCC1.CN(C)C=O.O>[C:1]1([C:7]#[C:8][C:9]([NH:27][C:28]2[CH:29]=[C:30]([CH:47]=[CH:48][CH:49]=2)[O:31][C:32]2[CH:33]=[CH:34][C:35]3[N:36]([CH:38]=[C:39]([NH:41][C:42]([CH:44]4[CH2:46][CH2:45]4)=[O:43])[N:40]=3)[N:37]=2)=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 69475Phenylpropiolic AcidHCID 57386059N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57505767N-(6-{3-[(3-phenylprop-2-ynoyl)amino]phenoxy}imidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamideYield 89%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-phenylprop-2-ynoic acid (85 mg, 0.581 mmol) in tetrahydrofuran (3 mL) were added isobutyl chlorocarbonate (76 μL, 0.581 mmol) and 4-methylmorpholine (80 μL, 0.727 mmol) under ice-cooling, a solution of N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (150 mg, 0.484 mmol) in N,N-dimethylformamide (3 mL) was further added thereto, and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the precipitated solid was filtrated and washed with water to give the title compound (188 mg, 89%) as a white powder.

Workup

  1. temperaturecooling
  2. filtrationthe precipitated solid was filtrated
  3. washwashed with water

Sources & evidence

ORD record
ord-3d5034bcc15e456ab89ea80177e5b25d
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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