HCID 66665632, compound → HCID 123671351, compound

HRID 406175Notes

Reaction equation

HRID 406175 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:13]=[C:12]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:11]=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCO.[Pd]>[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][C:16]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:13][CH:12]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:11][CH2:10]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 66665632HCID 66665632, compound

Product 1

HCID 123671351HCID 123671351, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A stirred solution of ethyl 6-(6,7-diphenyl-1,8-naphthyridin-2-yl)hexanoate (step 2)(280 mg, 0.660 mmol) in EtOH (10 ml) under an atmosphere of argon was treated with 10% palladium on carbon (70.2 mg), purged three times with nitrogen and placed under an atmosphere of hydrogen overnight. The mixture was filtered through Celite® (filter material) and the catalyst was washed with EtOAc (100 ml). The filtrate was concentrated in vacuo to yield the title compound as an off white solid. Purification of the crude product by chromatography on silica eluting with 0-100% EtOAc in iso-hexane afforded the title compound as a yellow oil. LC-MS Rt=1.46 mins; [M+H]+429.3, Method 2minLC_v002.

Workup

  1. custompurged three times with nitrogen
  2. filtrationThe mixture was filtered through Celite® (filter material)
  3. washthe catalyst was washed with EtOAc (100 ml)
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-83f52787e76c4df6b5abed10aa61185e
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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