HCID 46194726, compound → Cinacalcet

HRID 1915201Notes

Reaction equation

HRID 1915201 reaction equation
[C:1]1([C@H:11]([NH:13][CH2:14]/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H][H]>CO.Cl[Pd]Cl>[CH3:12][C@@H:11]([NH:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:24])([F:25])[F:26])[CH:18]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=12

Participants

5

Reactant 2

HCID 46194726HCID 46194726, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 156419CinacalcetYield 66.3%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 887MethanolSolvent

Procedure

A mixture of compound (VI) (3.0 g), PdCl2 (0.01 g), in methanol (10 mL) was pressurized with 1 bar hydrogen and stirred for 10 hrs at +25° C. The mixture was then filtered through a Celite® pad and concentrated to give Cinacalcet free base, compound (I) (2.0 g).

Workup

  1. filtrationThe mixture was then filtered through a Celite® pad
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-bbaf4f991f6b474d81d8092f7aeb25a3
Source dataset
uspto-grants-2013_12
Patent number
US08614353B2

Reaction notes

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