N,N-dibenzyl-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentanamine → 3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentanamine

HRID 1969588Notes

Reaction equation

HRID 1969588 reaction equation
C([N:8](CC1C=CC=CC=1)[CH:9]1[CH2:13][CH:12]([CH3:14])[CH:11]([C:15]2[N:19]3[C:20]4[CH:26]=[CH:25][NH:24][C:21]=4[N:22]=[CH:23][C:18]3=[N:17][CH:16]=2)[CH2:10]1)C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[CH:26]1[C:20]2[N:19]3[C:15]([CH:11]4[CH:12]([CH3:14])[CH2:13][CH:9]([NH2:8])[CH2:10]4)=[CH:16][N:17]=[C:18]3[CH:23]=[N:22][C:21]=2[NH:24][CH:25]=1

Participants

4

Reactant 1

HCID 58557511N,N-dibenzyl-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentanamine

Product 1

HCID 585571313-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentanamineYield 82%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of N,N-dibenzyl-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclo-pentanamine (1.84 g, 4.22 mmol, Preparation #52) in EtOH (50 mL) was added 20 wt % Pd(OH)2 on C (0.43 g, 0.61 mmol) and the resulting mixture was shaken under hydrogen pressure of about 50 psi on a Parr shaker at about 50° C. for about 2 h. The catalyst was filtered off using a pad of Celite®, 20 wt % Pd(OH)2 on C (0.43 g, 0.61 mmol) was added, and the mixture was shaken under hydrogen pressure of about 50 psi on a Parr shaker at about 50° C. for about 16 h. The catalyst was filtered off using a pad of Celite®, 20 wt % Pd(OH)2 on C (0.43 g, 0.61 mmol) was added, and the mixture was shaken under hydrogen pressure of about 50 psi on a Parr shaker at about 50° C. for about 4 h. The catalyst was filtered off using a pad of Celite® and the filtrate was concd under reduced pressure to yield 3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentanamine (0.88 g, 82%) as an off-white amorphous solid: LC/MS (Table 1, Method a) Rt=0.75 min and 0.87 min; MS m/z 256 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered off
  2. additionwas added
  3. stirringthe mixture was shaken under hydrogen pressure of about 50 psi on a Parr shaker at about 50° C. for about 16 h
  4. filtrationThe catalyst was filtered off
  5. additionwas added
  6. stirringthe mixture was shaken under hydrogen pressure of about 50 psi on a Parr shaker at about 50° C. for about 4 h
  7. filtrationThe catalyst was filtered off

Sources & evidence

ORD record
ord-faad632a798244fb9c76b1e0d9d07333
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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