Ammonia → HCID 57743032, compound

HRID 1896401Notes

Reaction equation

HRID 1896401 reaction equation
N.[Na].C([N:10]1[CH:14]=[C:13]([CH2:15][N:16]2[CH2:20][CH:19]([C:21]3[CH:26]=[C:25](F)[CH:24]=[C:23](F)[C:22]=3F)[CH2:18][C:17]2=[O:30])[CH:12]=[N:11]1)C1C=CC=CC=1.[NH4+].[Cl-]>C1COCC1.O>[C:21]1([CH:19]2[CH2:20][N:16]([CH2:15][C:13]3[CH:12]=[N:11][NH:10][CH:14]=3)[C:17](=[O:30])[CH2:18]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 15979452HCID 15979452, compound

Product 1

HCID 57743032HCID 57743032, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

In a 250 ml, three-necked flask fitted with a magnetic stirrer under inert atmosphere, 20 ml of liquid ammonia is condensed and sodium is added until the solution turns blue. A solution of 1-[(1-benzyl-1H-pyrazol-4-yl)methyl]-4-(2,3,5-trifluorophenyl)pyrrolidin-2-one 160 (1 g, 2.6 mmol) in THF (5 ml) is added and the mixture is stirred at −78° C. for 5 minutes. NH4Cl and water are added, ammonia is evaporated in vacuo and the aqueous phase is extracted with CH2Cl2. The combined organic phases are washed with brine, dried over MgSO4, filtered and concentrated to dryness. The residue is purified by preparative chromatography on C18 reversed phase (CH3CN/H2O/NH4HCO3, gradient) to afford 73 mg of 4-phenyl-1-(1H-pyrazol-4-ylmethyl)pyrrolidin-2-one 162.

Workup

  1. additionis added until the solution
  2. customammonia is evaporated in vacuo
  3. extractionthe aqueous phase is extracted with CH2Cl2
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue is purified by preparative chromatography on C18 reversed phase (CH3CN/H2O/NH4HCO3, gradient)

Sources & evidence

ORD record
ord-51570423687e42059478d5de1fd8fa54
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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