HCID 9953051, compound → [5-Amino-1-(4-fluorophenyl)-1H-pyrazol-4-yl][3-[3-(4-morpholinyl)propyl]phenyl]methanone

HRID 429352Notes

Reaction equation

HRID 429352 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:30])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[C:22][CH2:23][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:16]=1>C(O)C.[Pd]>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:30])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[CH:16]=1

Participants

4

Reactant 1

HCID 9953051HCID 9953051, compound

Product 1

HCID 11640131[5-Amino-1-(4-fluorophenyl)-1H-pyrazol-4-yl][3-[3-(4-morpholinyl)propyl]phenyl]methanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-amino-1-(4-fluorophenyl)-4-[3-(3-morpholin-4-ylprop-1-ynyl)-benzoyl]pyrazole (0.45 g, 1.0 mmol) [prepared as described in Example 1] and 5% Pd/C (0.07 g) in ethanol (20 ml) was stirred under hydrogen atmosphere. After 16 h, the reaction mixture was filtered through CELITE® and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography (elution gradient, EtOAc-15% MeOH/EtOAc with 0.2% NH4OH). The product was converted to the hydrochloride salt and recrystallized from a mixture of methanol/ethyl acetate to give 5-amino-1-(4-fluorophenyl)-4-[3-(3-morpholin-4-ylpropyl)benzoyl]pyrazole.HCl (0.3 g, mpt. 211.9-212.6° C.) as a solid.

Workup

  1. filtrationthe reaction mixture was filtered through CELITE®
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified by flash chromatography (elution gradient, EtOAc-15% MeOH/EtOAc with 0.2% NH4OH)
  4. customrecrystallized from a mixture of methanol/ethyl acetate

Sources & evidence

ORD record
ord-892f58978e4b420f9b3acf89180d0121
Source dataset
uspto-grants-2001_11
Patent number
US06316466B1

Reaction notes

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