Sodium Bicarbonate → HCID 58459253, compound

HRID 2036621Notes

Reaction equation

HRID 2036621 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]([CH3:27])[C:9]([NH:11][C:12]1[C:13]([NH:18][C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)=[N:14][CH:15]=[CH:16][CH:17]=1)=O)([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+]>CC(O)=O>[F:26][C:21]1[CH:20]=[C:19]([N:18]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=[C:9]2[CH:8]([NH:7][C:6](=[O:28])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:27])[CH:24]=[C:23]([F:25])[CH:22]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 68225760HCID 68225760, compound

Product 1

HCID 58459253HCID 58459253, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of (S)-tert-butyl-1-(2-(3,5-difluorophenylamino)pyridine-3-ylamino)-1-oxopropan-2-ylcarbamate (1.7 g, 4.33 mmol) in AcOH (12 mL) was stirred at 100° C. overnight. After completion of the reaction the mixture was cooled to rt and basified with satd. sodium bicarbonate solution (60 mL). The organic layer was then extracted with EtOAc (150 mL), dried over sodium sulfate an concentrated in vacuo to provide tert-butyl 1-(3-(3,5-Difluorophenyl)-3H-imidazo[4,5-b]pyridin-2-yl)-ethylcarbamate. The crude product was used without further purification.

Workup

  1. customAfter completion of the reaction the mixture
  2. extractionThe organic layer was then extracted with EtOAc (150 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationan concentrated in vacuo

Sources & evidence

ORD record
ord-2fb06a5569f8474294d45be6a9b22c64
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

Loading…