HCID 86717954, compound → HCID 86717953, compound

HRID 2275879Notes

Reaction equation

HRID 2275879 reaction equation
[F:1][C:2]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:18][C@H:19]3[CH2:23][CH2:22][N:21](C(OCC4C=CC=CC=4)=O)[CH2:20]3)=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1>C(O)C.[OH-].[Pd+2].[OH-]>[F:1][C:2]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:18][C@H:19]3[CH2:23][CH2:22][NH:21][CH2:20]3)=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 86717954HCID 86717954, compound

Product 1

HCID 86717953HCID 86717953, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

130 mg of benzyl (3S)-3-[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}-carbonyl)amino]pyrrolidine-1-carboxylate (Example 115A; 0.250 mmol) were initially charged in 60 ml of ethanol, 17.5 mg 20% palladium-(II) hydroxide (0.025 mmol, 0.1 equivalents) were added and the mixture was hydrogenated under hydrogen standard pressure for two hours. The reaction mixture was filtered and concentrated and the residue was purified by preparative HPLC. This gave 42 mg (44% of theory) of the title compound.

Workup

  1. customfor two hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-513e193950ce4b0e9eb88a00346a7b5a
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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