HCID 71204713, compound → HCID 71204714, compound

HRID 712896Notes

Reaction equation

HRID 712896 reaction equation
[F:1][C:2]1([F:33])[CH2:6][N:5](CC2C=CC=C(C(F)(F)F)C=2)[C@@H:4]([C:18]([NH:20][C@H:21]([C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)[CH3:22])=[O:19])[CH2:3]1>CO.Cl.[Pd]>[F:33][C:2]1([F:1])[CH2:6][NH:5][C@@H:4]([C:18]([NH:20][C@H:21]([C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)[CH3:22])=[O:19])[CH2:3]1

Participants

5

Reactant 1

HCID 71204713HCID 71204713, compound

Product 1

HCID 71204714HCID 71204714, compoundYield 136.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A suspension of methyl 4-((S)-1-((R)-4,4-difluoro-1-(3-(trifluoromethyl)benzyl)pyrrolidine-2-carboxamido)ethyl)benzoate (D164) (33 mg) and 10% w Pd/C (5 mg) in MeOH (5 ml) and 1M HCl (0.5 ml) was stirred under a constant current of H2 for 3 hrs. Catalyst was filtered off and solvent evaporated to afford a residue which was triturated with cHex and filtered to afford the title compound (D165) (30 mg).

Workup

  1. filtrationCatalyst was filtered off
  2. customsolvent evaporated
  3. customto afford a residue which
  4. customwas triturated with cHex
  5. filtrationfiltered

Sources & evidence

ORD record
ord-aab5aa6e38a74a828cfdd9078e1d071f
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

Loading…