Hydrochloric Acid → HCID 178472391, compound

HRID 518635Notes

Reaction equation

HRID 518635 reaction equation
C([O:8][CH2:9][CH2:10][O:11][C:12]1[N:17]=[CH:16][C:15]2[NH:18]/[C:19](=[N:32]\[C:33](=[O:41])[C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=3)/[N:20]([C@@H:21]3[CH2:26][CH2:25][C@H:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:22]3)[C:14]=2[CH:13]=1)C1C=CC=CC=1.Cl>CCO.[Pd]>[F:40][C:36]1[CH:35]=[C:34]([CH:39]=[CH:38][CH:37]=1)[C:33](/[N:32]=[C:19]1/[N:20]([C@@H:21]2[CH2:22][CH2:23][C@H:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:25][CH2:26]2)[C:14]2[CH:13]=[C:12]([O:11][CH2:10][CH2:9][OH:8])[N:17]=[CH:16][C:15]=2[NH:18]/1)=[O:41]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178472392HCID 178472392, compound

Product 1

HCID 178472391HCID 178472391, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A round bottom flask under nitrogen was charged with cis-ethyl 4-((E)-6-(2-(benzyloxy)ethoxy)-2-(3-fluorobenzoylimino)-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)cyclohexanecarboxylate (2.5 g, 4.46 mmol), 10% Pd/C (0.712 g, 0.669 mmol), EtOH (8.92 mL), and concentrated HCl (0.372 mL, 4.46 mmol). The reaction mixture was stirred under an atmosphere of hydrogen for 24 hours. The mixture was diluted with EtOH (50 mL) and filtered through Celite® brand filter aid. The cake was washed with DCM (50 mL), EtOH (50 mL), and MeOH (50 mL), and the filtrate was concentrated to dryness. The residue was dissolved in 2% MeOH/DCM (100 mL) and washed with aqueous NaHCO3 (50 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford cis-ethyl 4-((E)-2-(3-fluorobenzoylimino)-6-(2-hydroxyethoxy)-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)cyclohexanecarboxylate as a tan solid (2.1 g, 100% yield). MS m/z=471.2 [M+H]. Calc'd for C24H27FN4O5: 470.2.

Workup

  1. filtrationfiltered through Celite® brand
  2. filtrationfilter aid
  3. washThe cake was washed with DCM (50 mL), EtOH (50 mL), and MeOH (50 mL)
  4. concentrationthe filtrate was concentrated to dryness
  5. dissolutionThe residue was dissolved in 2% MeOH/DCM (100 mL)
  6. washwashed with aqueous NaHCO3 (50 mL)
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-67ac1d74fe44468b8671d815a1564928
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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