Sodium Hydroxide → HCID 58010221, compound

HRID 2204608Notes

Reaction equation

HRID 2204608 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH:3]1[C:18]1[N:22]2[C:23]3[CH:29]=[CH:28][N:27](S(C4C=CC(C)=CC=4)(=O)=O)[C:24]=3[N:25]=[CH:26][C:21]2=[N:20][CH:19]=1.[OH-].[Na+]>O1CCOCC1>[CH:29]1[C:23]2[N:22]3[C:18]([CH:3]4[CH:2]([CH3:1])[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)=[O:9])[CH2:4]4)=[CH:19][N:20]=[C:21]3[CH:26]=[N:25][C:24]=2[NH:27][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58010113HCID 58010113, compound

Product 1

HCID 58010221HCID 58010221, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of benzyl 4-methyl-3-(3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)piperidine-1-carboxylate (0.93 g, 1.7 mmol) in 1,4-dioxane (20 mL) was added aqueous NaOH (2 N, 1.0 mL), and the resulting mixture was heated at about 90° C. for about 80 min. The solvents were removed under reduced pressure and the residue was treated with saturated aqueous NH4Cl (26 mL) and extracted with EtOAc (2×30 mL). The combined organic extracts were washed with brine (20 mL), dried over anhydrous MgSO4, filtered, and concentrated to yield the crude product as a brown amorphous solid. The material was purified by silica gel chromatography eluting with a gradient of 5-100% MeOH/DCM to give benzyl 3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylpiperidine-1-carboxylate (0.55 g, 83%) as a yellow solid: LC/MS (Table 2, Method a) Rt=1.94 min; MS m/z: 390 (M+H)+.

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionthe residue was treated with saturated aqueous NH4Cl (26 mL)
  3. extractionextracted with EtOAc (2×30 mL)
  4. washThe combined organic extracts were washed with brine (20 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield the crude product as a brown amorphous solid
  9. customThe material was purified by silica gel chromatography
  10. washeluting with a gradient of 5-100% MeOH/DCM

Sources & evidence

ORD record
ord-d0c8e419def84070b7af4bac893033a5
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

Loading…