Morpholine → HCID 9887680, compound

HRID 429360Notes

Reaction equation

HRID 429360 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH2:7][C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[N:11]=[CH:10][C:9]=1[C:20](=[O:31])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27](=[O:30])[CH2:28]Br)[CH:22]=1>CN(C)C=O.[Cl-].[Na+].O>[NH2:7][C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[N:11]=[CH:10][C:9]=1[C:20](=[O:31])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([CH2:28][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:30])[CH:22]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 22262806HCID 22262806, compound

Product 1

HCID 9887680HCID 9887680, compoundYield 21.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of morpholine (0.25 ml, 2.79 mmol) in dimethylformamide (5 ml) was added a solution of 5-amino-4-[3-(2-bromoacetyl)benzoyl]-1-(4-fluorophenyl)pyrazole (0.22 g, 0.56 mmol) in dimethylformamide (5 ml). After 16 h, the reaction mixture was poured into brine and the product was extracted into ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (elution gradient: ethyl acetate-10% methanol/ethyl acetate) to give 5-amino-1-(4-fluorophenyl)-4-[3-(morpholin-4-ylmethylcarbonyl)benzoyl]pyrazole (0.05 g) as a solid.

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (elution gradient: ethyl acetate-10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-e5503572277c48e380acd8864c038506
Source dataset
uspto-grants-2001_11
Patent number
US06316466B1

Reaction notes

Loading…