Formic Acid → Cinacalcet

HRID 1915200Notes

Reaction equation

HRID 1915200 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.C(O)=O>C(O)C.C1(C)C=CC=CC=1.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

6

Reactant 2

HCID 284Formic AcidHCID 46194726HCID 46194726, compound

Product 1

HCID 156419CinacalcetYield 66.3%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of compound (VI) (3.0 g), PdCl2 (0.01 g) in ethanol (10 mL) was heated up to reflux temperature and added in 5 hrs with formic acid (0.3 g). The mixture was then cooled down, diluted with toluene and washed with 30% w/w aqueous sodium hydroxide until neutrality. The organic layer was dried and concentrated to give Cinacalcet free base, compound (I) (2.0 g).

Workup

  1. temperaturewas heated up
  2. temperatureto reflux temperature
  3. temperatureThe mixture was then cooled down
  4. washwashed with 30% w/w aqueous sodium hydroxide until neutrality
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1db06e5abed0444cb2afeb46359ee0a2
Source dataset
uspto-grants-2013_12
Patent number
US08614353B2

Reaction notes

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