HCID 131727919, compound → HCID 131727921, compound

HRID 2242655Notes

Reaction equation

HRID 2242655 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C@H:8]([C:26]([N:28]1[CH2:32][CH2:31][C:30]([F:34])([F:33])[CH2:29]1)=[O:27])[C@H:9]([CH:11]1[CH2:16][CH2:15][C:14]([C:17]2[N:22]3[N:23]=[CH:24][N:25]=[C:21]3[CH:20]=[CH:19][CH:18]=2)=[CH:13][CH2:12]1)[CH3:10])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO.C(O)(=O)C>[C:1]([O:5][C:6](=[O:35])[NH:7][C@H:8]([C:26]([N:28]1[CH2:32][CH2:31][C:30]([F:34])([F:33])[CH2:29]1)=[O:27])[C@H:9]([CH:11]1[CH2:12][CH2:13][CH:14]([C:17]2[N:22]3[N:23]=[CH:24][N:25]=[C:21]3[CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:16]1)[CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 2

HCID 131727919HCID 131727919, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131727921HCID 131727921, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The material from Step B (0.13 g, 0.27 mmol) was hydrogenated at 50 psi hydrogen in the presence of 10% palladium on carbon (0.13 g) in methanol (5 mL) containing 30 drops of acetic acid using a Parr shaker. After 1 h, the reaction mixture was filtered by passage through a syringe filter. The filtrate was concentrated and the residue was dissolved in chloroform and washed with saturated aqueous sodium bicarbonate. The organic layer was dried (anhydrous sodium sulfate) and concentrated in vacuo. The residue was purified by silica gel chromatography (0-5% methanol in dichloromethane) gradient to afford the title compound. LC/MS 492.1 (M+1).

Workup

  1. filtrationthe reaction mixture was filtered by passage through a syringe
  2. filtrationfilter
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue was dissolved in chloroform
  5. washwashed with saturated aqueous sodium bicarbonate
  6. dry with materialThe organic layer was dried (anhydrous sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (0-5% methanol in dichloromethane) gradient

Sources & evidence

ORD record
ord-0064a4eb18944683906fff85ba32fedf
Source dataset
uspto-grants-2010_03
Patent number
US07671073B2

Reaction notes

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