Ethanol → HCID 58382138, compound

HRID 1628020Notes

Reaction equation

HRID 1628020 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][N:11]=[C:10]3[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=[CH:21][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].CCO>O1CCOCC1>[CH:1]1([NH:7][C:8]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=[C:10]3[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=[CH:21][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 583819901H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-(cyclohexylamino)-1-[[2-(trimethylsilyl)ethoxy]methyl]-, ethyl ester

Product 1

HCID 58382138HCID 58382138, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the suspension of ethyl 4-(cyclohexylamino)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.77 g, 1.9 mmol) in 1,4-dioxane (12 mL) was added aquoeous NaOH (1 N, 12 mL, 12 mmol). The mixture was stirred at rt for about 48 h. To the mixture was added EtOH (1 mL) and the mixture was heated at about 50° C. for about 24 h. The mixture was concentrated under reduced pressure and aqueous HCl (0.5 M, 10 mL) was added and the mixture extracted with EtOAc (25 mL). The solid in the organic layer was collected by vacuum filtration. The filtrate and aqueous layer were recombined and separated. The solid was dissolved in EtOAc (˜150 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo and dried under reduced pressure at about rt to give 4-(cyclohexylamino)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (0.713 g, 99%): LC/MS (Table 2, Method b) Rt=2.74 min.; MS m/z: 390 (M+H)+.

Workup

  1. temperaturethe mixture was heated at about 50° C. for about 24 h
  2. concentrationThe mixture was concentrated under reduced pressure and aqueous HCl (0.5 M, 10 mL)
  3. additionwas added
  4. extractionthe mixture extracted with EtOAc (25 mL)
  5. filtrationThe solid in the organic layer was collected by vacuum filtration
  6. customseparated
  7. dissolutionThe solid was dissolved in EtOAc (˜150 mL)
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customdried under reduced pressure at about rt

Sources & evidence

ORD record
ord-07e280b002a74fb1862246876491f8fc
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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