HCID 11197984, compound → HCID 58911277, compound

HRID 2358253Notes

Reaction equation

HRID 2358253 reaction equation
[O:1]=[C:2]1[CH2:6][CH:5]([C:7]2[CH:12]=[C:11]([F:13])[C:10]([F:14])=[C:9]([F:15])[CH:8]=2)[CH2:4][N:3]1[CH2:16][N:17]1[CH:21]=[C:20](C#N)[N:19]=[CH:18]1.[NH3:24].[CH3:25]O>[Pd]>[NH2:24][CH2:25][C:21]1[N:17]([CH2:16][N:3]2[CH2:4][CH:5]([C:7]3[CH:12]=[C:11]([F:13])[C:10]([F:14])=[C:9]([F:15])[CH:8]=3)[CH2:6][C:2]2=[O:1])[CH:18]=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 11197984HCID 11197984, compoundHCID 21705897Ammonia methanol

Product 1

HCID 58911277HCID 58911277, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a 250 ml parr apparatus, Pd/C (0.1 g, 10% w/w) is added onto a solution of the enantiomerically pure (+)-1-{[2-oxo-4-(3,4,5-trifluorophenyl)pyrrolidin-1-yl]methyl}-1H-imidazole-4-carbonitrile 79 (0.2 g, 0.624 mmol) in NH3/MeOH (3 M, 30 ml) and the suspension is stirred under an hydrogen pressure (50 psi) for 6 h. The reaction mixture is concentrated in vacuo, dissolved in AcOEt, dried over MgSO4, filtered and concentrated in vacuo to afford 0.14 g of crude 1-(5-aminomethyl-imidazol-1-ylmethyl)-4-(3,4,5-trifluoro-phenyl)-pyrrolidin-2-one a34 which is used as such in the next step.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutiondissolved in AcOEt
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ddf34bed9c64a97845fc72123e1f0ee
Source dataset
uspto-grants-2010_07
Patent number
US07763644B2

Reaction notes

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