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4-Methylmorpholine → N-[5-(6-cyanoimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide

HRID 539753
Notes
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Reaction equation

HRID 539753 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:24]([F:27])([F:26])[F:25])=[C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=3)=[CH:10][N:4]2[N:3]=1.[Cu](C#N)[C:29]#[N:30].CN1CCOCC1>CCOCC.C([O-])(O)=O.[Na+]>[C:29]([C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:24]([F:27])([F:26])[F:25])=[C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=3)=[CH:10][N:4]2[N:3]=1)#[N:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 86667850N-(5-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-(trifluoromethyl)phenyl)pivalamideHCID 178418260HCID 178418260, compound

Product 1

HCID 67983247N-[5-(6-cyanoimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamideYield 26%

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
215 °C

Procedure

An 8 mL vial is charged with N-[5-(6-chloroimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide (0.059 g, 0.15 mmol), copper cyanide (0.035 g, 0.3 mmol), and 4-methylmorpholine (0.43 mL). The mixture is stirred at 215° C. for 4 hr in the microwave, then cooled, diluted with Et2O, sat. aqueous NaHCO3 and the biphasic mixture is filtered. Organics are collected and aqueous layer is extracted twice more with Et2O. Organics are combined, dried, concentrated, and purified by prep plate TLC (1:1 Hex:EtOAc) to give the title compound (15 mg, 26% yield). LCMS m/z=388.5 [M+H]+, tR=2.56 min. (compound same as Example 173)

Workup

  1. temperaturecooled
  2. filtrationthe biphasic mixture is filtered
  3. customOrganics are collected
  4. extractionaqueous layer is extracted twice more with Et2O
  5. customdried
  6. concentrationconcentrated
  7. custompurified by prep plate TLC (1:1 Hex:EtOAc)

Sources & evidence

ORD record
ord-012bf39a62ff45a6969a4a1757144da0
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08871767B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes