HCID 69939882, compound → HCID 66787770, compound

HRID 1428514Notes

Reaction equation

HRID 1428514 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][N:17]3[C:20]([CH2:23][CH:24]4[CH2:26][CH2:25]4)=[N:21][N:22]=[C:16]3[C:15]=2[CH3:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][N:17]3[C:20]([CH2:23][CH:24]4[CH2:25][CH2:26]4)=[N:21][N:22]=[C:16]3[C:15]=2[CH3:27])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 69939882HCID 69939882, compound

Product 1

HCID 66787770HCID 66787770, compoundYield 35.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of intermediate D99 (0.606 g, 1.645 mmol) in EtOH (35 ml) was hydrogenated in a H-Cube® reactor (1 ml/min, Pd/C 10% cartridge, full H2 mode, 80° C.). The solvent was concentrated in vacuo and the residue was purified by column chromatography (silica gel; EtOAc/7M solution of NH3 in MeOH up to 6% as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate D100 (0.214 g, 35%).

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customthe residue was purified by column chromatography (silica gel; EtOAc/7M solution of NH3 in MeOH up to 6% as eluent)
  3. customThe desired fractions were collected
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-582c0b23536d4f4686c1f18eed379da4
Source dataset
uspto-grants-2015_01
Patent number
US08937060B2

Reaction notes

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