HCID 69044992, compound → HCID 69043464, compound

HRID 925073Notes

Reaction equation

HRID 925073 reaction equation
[O:1]=[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([CH2:12][CH:13]2[CH2:18][N:17](C(OCC3C=CC=CC=3)=O)[CH2:16][CH2:15][N:14]2[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[N:4][NH:3]1>O1CCCC1.[Pd]>[O:1]=[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([CH2:12][CH:13]2[CH2:18][NH:17][CH2:16][CH2:15][N:14]2[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[N:4][NH:3]1

Participants

4

Reactant 1

HCID 69044992HCID 69044992, compound

Product 1

HCID 69043464HCID 69043464, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of EXAMPLE 257D (0.77 g, 1.6 mmol) in tetrahydrofuran (100 ml) was treated with 10% palladium on carbon (85 mg, 0.8 mmol) at room temperature under hydrogen (balloon) overnight. The catalyst was removed by filtration, and the filtrate was concentrated. The residue was purified by flash chromatography (0-15% gradient of methanol in CH2Cl2) to provide the title compound. MS (DCI/NH3) m/z 349 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash chromatography (0-15% gradient of methanol in CH2Cl2)

Sources & evidence

ORD record
ord-ad5886167b9448519c9c87b74b4fbe92
Source dataset
uspto-grants-2016_03
Patent number
US09283222B2

Reaction notes

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