Benzyl 4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidine-1-carboxylate → Bms-973013

HRID 469286Notes

Reaction equation

HRID 469286 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[N:3]1[CH:11]1[CH2:16][CH2:15][N:14](C(OCC2C=CC=CC=2)=O)[CH2:13][CH2:12]1.[H][H]>CO.[Pd]>[NH:14]1[CH2:13][CH2:12][CH:11]([N:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:10][C:2]2=[O:1])[CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 46853855Benzyl 4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 22293182Bms-973013

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

690 g (1.96 mol) benzyl 4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidine-1-carboxylate were dissolved in 5.4 L methanol and hydrogenated with the addition of 46 g Pd/C (10%; 6.6% by weight) at 60° C. under a hydrogen pressure of 60 psi until all the hydrogen had been taken up. The catalyst was filtered off. 4 L methanol were distilled off from the filtrate. 2 L methylcyclohexane were added and a further 1.5 L solvent were distilled off. The suspension thus obtained was suction filtered, the residue was washed with methylcyclohexane and dried at 40° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. distillation4 L methanol were distilled off from the filtrate
  3. addition2 L methylcyclohexane were added
  4. distillationa further 1.5 L solvent were distilled off
  5. customThe suspension thus obtained
  6. washthe residue was washed with methylcyclohexane
  7. customdried at 40° C.

Sources & evidence

ORD record
ord-317b453bc5e54d53a9cf9d239419456e
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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