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

HRID 1969853Notes

Reaction equation

HRID 1969853 reaction equation
C([N:8](CC1C=CC=CC=1)[CH:9]1[CH2:13][CH:12]([C:14]2[N:18]3[C:19]4[CH:25]=[CH:24][N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:20]=4[N:21]=[CH:22][C:17]3=[N:16][CH:15]=2)[CH:11]([CH3:34])[CH2:10]1)C1C=CC=CC=1.[H][H]>C(O)C(F)(F)F.[OH-].[OH-].[Pd+2]>[CH3:34][CH:11]1[CH:12]([C:14]2[N:18]3[C:19]4[CH:25]=[CH:24][N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:20]=4[N:21]=[CH:22][C:17]3=[N:16][CH:15]=2)[CH2:13][CH:9]([NH2:8])[CH2:10]1

Participants

5

Reactant 2

HCID 58557169N,N-dibenzyl-3-methyl-4-(3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)cyclopentanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 585575733-methyl-4-(3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)cyclopentanamineYield 98%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 64092,2,2-TrifluoroethanolSolvent

Procedure

To a solution of N,N-dibenzyl-3-methyl-4-(3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)cyclopentanamine (3.0 g, 5.30 mmol) in trifluoroethanol (200 mL) was added 20% wet palladium hydroxide on carbon (0.6 g, 4.27 mmol). The mixture was stirred under 40 psi of hydrogen at about 50° C. for about 90 min. The catalyst was removed by filtration through a pad of Celite® and the filtrate was concd under reduced pressure to yield 3-methyl-4-(3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)cyclopentanamine (2.0 g, 98% yield) as a brown amorphous solid. LC/MS (Table 1, Method a) Rt=1.86 min; MS m/z 386 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite®

Sources & evidence

ORD record
ord-0d44545cb27d47e7a31b6104e05cfe6f
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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