[(S)-1-(2-Phenylaminopyridin-3-ylcarbamoyl)propyl]carbamic acid tert-butyl ester → [(S)-1-(3-Phenyl-3H-imidazo[4,5-b]pyridin-2-yl)propyl]carbamic acid tert-butyl ester

HRID 242897Notes

Reaction equation

HRID 242897 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:11](=O)[NH:12][C:13]1[C:14]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:15][CH:16]=[CH:17][CH:18]=1)[CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:11]1[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[N:12]=1)[CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 68157992[(S)-1-(2-Phenylaminopyridin-3-ylcarbamoyl)propyl]carbamic acid tert-butyl ester

Product 1

HCID 68157696[(S)-1-(3-Phenyl-3H-imidazo[4,5-b]pyridin-2-yl)propyl]carbamic acid tert-butyl esterYield 83.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of [(S)-1-(2-phenylaminopyridin-3-ylcarbamoyl)propyl]carbamic acid tert-butyl ester (4.32 mmol) in AcOH (30 mL) was heated at 70° C. for 3 h. After cooling to RT, the volatiles were removed under reduced pressure and the residue partitioned between DCM and a saturated aqueous solution of NaHCO3. The aqueous phase was extracted with DCM (×3) and the combined organic fractions washed with water, dried (Na2SO4) and concentrated in vacuo to afford the title compound as an oil (1.27 g, crude material). LCMS (Method C): RT 3.24 min [M+H]+ 353.4.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customthe residue partitioned between DCM
  3. extractionThe aqueous phase was extracted with DCM (×3)
  4. washthe combined organic fractions washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-91bcea7ae93649709a2fab2393d8c2a9
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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