Sodium Hydroxide → HCID 178420346, compound

HRID 1969905Notes

Reaction equation

HRID 1969905 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[CH2:14][CH2:13][CH:12]([C:15]2[N:19]3[C:20]4[CH:26]=[CH:25][N:24](S(C5C=CC(C)=CC=5)(=O)=O)[C:21]=4[N:22]=[CH:23][C:18]3=[N:17][CH:16]=2)[CH2:11][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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:9]1[CH2:14][CH2:13][C@@H:12]([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)[CH2:11][CH2:10]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58557876HCID 58557876, compound

Product 1

HCID 178420346HCID 178420346, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

N,N-dibenzyl-4-(3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)cyclohexanamine (5.6 g, 9.5 mmol) was dissolved in 1,4-dioxane (80 mL). Aqueous NaOH (2 N, 47.5 mL, 95 mmol) was added and the reaction mixture was heated at about 60° C. for about 120 min. The organic solvent was removed under reduced pressure and the residue was extracted with 2-methyl tetrahydrofuran (300 mL). The aqueous layer was extracted with 2-methyl tetrahydrofuran (3×50 mL). The combined organic extracts were washed with brine (30 mL), dried over anhydrous Na2SO4 and concd under reduced pressure. To the residue was added EtOAc (500 mL). The solid was removed by filtration and the filtrate was dried over anhydrous Na2SO4 and concd under reduced pressure. Purification by silica gel flash chromatography eluting with a gradient of 1-8% MeOH in EtOAc yielded (cis)-N,N-dibenzyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)cyclohexanamine (1.0 g, 24%): LC/MS (Table 1, Method a) Rt=2.48 min; MS m/z 436 (M+H)+.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. extractionthe residue was extracted with 2-methyl tetrahydrofuran (300 mL)
  3. extractionThe aqueous layer was extracted with 2-methyl tetrahydrofuran (3×50 mL)
  4. washThe combined organic extracts were washed with brine (30 mL)
  5. dry with materialdried over anhydrous Na2SO4 and concd under reduced pressure
  6. additionTo the residue was added EtOAc (500 mL)
  7. customThe solid was removed by filtration
  8. dry with materialthe filtrate was dried over anhydrous Na2SO4 and concd under reduced pressure
  9. customPurification by silica gel flash chromatography
  10. washeluting with a gradient of 1-8% MeOH in EtOAc

Sources & evidence

ORD record
ord-56d1db16da5d4d418aa24e6d66f29759
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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