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

HRID 1969587Notes

Reaction equation

HRID 1969587 reaction equation
[CH2:1]([N:8]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH:9]1[CH2:13][CH:12]([C:14]2[N:18]3[C:19]4[CH:25]=[CH:24][N:23](S(C5C=CC(C)=CC=5)(=O)=O)[C:20]=4[N:21]=[CH:22][C:17]3=[N:16][CH:15]=2)[CH:11]([CH3:36])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[CH2:37]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:9]1[CH2:10][CH:11]([CH3:36])[CH:12]([C:14]2[N:18]3[C:19]4[CH:25]=[CH:24][NH:23][C:20]=4[N:21]=[CH:22][C:17]3=[N:16][CH:15]=2)[CH2:13]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58557179N,N-Dibenzyl-3-methyl-4-(3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)cyclopentan-amine

Product 1

HCID 58557511N,N-dibenzyl-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentanamineYield 56%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

N,N-Dibenzyl-3-methyl-4-(3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)cyclopentan-amine (4.47 g, 7.58 mmol, Preparation #51) was dissolved in 1,4-dioxane (40 mL). NaOH (2 N aqueous, 4 mL) was added and the reaction mixture was heated at about 90° C. for about 80 min. The organic solvent was removed under reduced pressure and the residue was treated with saturated aqueous NH4Cl (70 mL) and extracted with DCM (2×60 mL). The combined organic extracts were washed with brine (70 mL), dried over anhydrous MgSO4 and concd under reduced pressure. Purification by silica gel flash chromatography eluting with a gradient of 0-8% MeOH in DCM yielded N,N-dibenzyl-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentan-amine (1.84 g, 56%) as a yellow oil: LC/MS (Table 1, Method a) Rt=2.31 min; MS m/z 436 (M+H)+.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. additionthe residue was treated with saturated aqueous NH4Cl (70 mL)
  3. extractionextracted with DCM (2×60 mL)
  4. washThe combined organic extracts were washed with brine (70 mL)
  5. dry with materialdried over anhydrous MgSO4 and concd under reduced pressure
  6. customPurification by silica gel flash chromatography
  7. washeluting with a gradient of 0-8% MeOH in DCM

Sources & evidence

ORD record
ord-2105809c55c54f35bf0644dd9f5d1e7d
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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