Morpholine → HCID 22258163, compound

HRID 1610837Notes

Reaction equation

HRID 1610837 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([CH3:10])[NH:6][C:7]=1[CH2:8][CH3:9])[CH3:2].[F:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1.N1CCOCC1>C(#N)C.CO>[CH2:1]([C:3]1[N:4]=[C:5]([CH2:10][C:16]([C:15]2[CH:19]=[CH:20][C:12]([F:11])=[CH:13][CH:14]=2)=[O:17])[NH:6][C:7]=1[CH2:8][CH3:9])[CH3:2]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 678794-Fluorobenzoyl chlorideHCID 22258241HCID 22258241, compound

Product 1

HCID 22258163HCID 22258163, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

The compound is prepared as described in example X (step 4) with 800 mg (5.79 mmol) of 4,5-Diethyl-2-methyl-1H-imidazole (example XXVII, step 1), 2.75 g (17.36 mmol) of 4-fluorobenzoyl chloride and 1.93 g (19.10 mmol) of TEA in 15 ml acetonitrile. The crude intermediate (1.30 g, 2.58 mmol) is dissolved in 10 ml methanol under argon. 1.12 g (12.88 mmol) of morpholine are added dropwise to the solution. The mixture is refluxed for 10 minutes. The solvent is evaporated under argon and the residue is purified over silica (eluent: dichlormethane/methanol 50:1). The solvent is evaporated under vacuum to yield 572 mg (82.6% of th.).

Workup

  1. customThe compound is prepared
  2. temperatureThe mixture is refluxed for 10 minutes
  3. customThe solvent is evaporated under argon
  4. customthe residue is purified over silica (eluent: dichlormethane/methanol 50:1)
  5. customThe solvent is evaporated under vacuum
  6. customto yield 572 mg (82.6% of th.)

Sources & evidence

ORD record
ord-a46866d13f2f4294bd8634dd7d70a296
Source dataset
uspto-grants-2006_01
Patent number
US06984646B2

Reaction notes

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