Sodium Hydroxide → HCID 69439940, compound

HRID 1890645Notes

Reaction equation

HRID 1890645 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH:22]3[CH2:27][CH2:26][N:25]([C:28]([CH:30]4[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]4)=[O:29])[CH2:24][CH2:23]3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].C(OCC)(=O)C.Cl.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH:22]3[CH2:27][CH2:26][N:25]([C:28]([CH:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)=[O:29])[CH2:24][CH2:23]3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 23156171HCID 23156171, compound

Product 1

HCID 69439940HCID 69439940, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-[4-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-ylmethyl)phenylamino]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylcarbonyl]piperidine (0.311 g, 0.54 mmol) obtained in Step 1 in chloroform (5.0 mL) was added with a 4 mol/L hydrogen chloride-ethyl acetate solution (2.0 mL) followed by stirring at room temperature for 1 hour. The reaction mixture was added with a 2 mol/L aqueous sodium hydroxide solution to control the pH to 12 and extracted with chloroform three times. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained crystals were added with diisopropyl ether followed by stirring under reflux for 1 hour. The crystals were collected by filtration and dried under reduced pressure to obtain Compound 147 (0.153 g, 0.32 mmol, 60%).

Workup

  1. extractionextracted with chloroform three times
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionThe obtained crystals were added with diisopropyl ether
  5. stirringby stirring
  6. temperatureunder reflux for 1 hour
  7. filtrationThe crystals were collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-9b00533878a84ecf941baad7edd4603f
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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