HCID 59754260, compound → HCID 59754234, compound

HRID 751142Notes

Reaction equation

HRID 751142 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 2h, 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. filtrationAfter 2h, the 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-7ab978cd4ff9401ea7b2bc946d1533a6
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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