HCID 59754260, compound → HCID 59754234, compound

HRID 501627Notes

Reaction equation

HRID 501627 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[C@H:15]([C:16]([F:19])([F:18])[F:17])[C@@H:14]3[C@@H:20]([N:23]=[N+]=[N-])[CH2:21][CH2:22][N:13]3[C:12]2=[O:26])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H][H]>CCO.[Pt](=O)=O>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[C@H:15]([C:16]([F:18])([F:19])[F:17])[C@@H:14]3[C@@H:20]([NH2:23])[CH2:21][CH2:22][N:13]3[C:12]2=[O:26])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 2

HCID 59754260HCID 59754260, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59754234HCID 59754234, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To 69B (15.0 mg, 0.0391 mmol) in EtOH (1 mL) was added platinum (IV) oxide (5 mg) and hydrogen was bubbled through the system for 10 min. The hydrogen outlet was removed and the system was stirred under a hydrogen atmosphere. After 2 h, the reaction was filtered through celite and concentrated. The resulting residue was purified via preparative HPLC (YMC ODS C-18, 21×100 mm, eluting with 50-100% solvent B (A=90% H2O-10% MeOH and B=10% H2O-90% MeOH) over 10 min; Flow rate at 40 mL/min; UV detection at 220 nm) to provide the title compound (6.00 mg) as a clear film. MS: m/z 419 [M+HCO3]−

Workup

  1. customwas bubbled through the system for 10 min
  2. customThe hydrogen outlet was removed
  3. filtrationthe reaction was filtered through celite and
  4. concentrationconcentrated
  5. customThe resulting residue was purified via preparative HPLC (YMC ODS C-18, 21×100 mm
  6. washeluting with 50-100% solvent B (A=90% H2O-10% MeOH and B=10% H2O-90% MeOH) over 10 min

Sources & evidence

ORD record
ord-40a95ccf8afe42bb8842956098bad65a
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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