HCID 86710391, compound → HCID 86710390, compound

HRID 1398403Notes

Reaction equation

HRID 1398403 reaction equation
[CH3:1][CH:2]([CH3:34])[CH2:3][C@H:4]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:5][O:6][C:7]1[C:8]([C:23]([CH3:25])=[CH2:24])=[CH:9][C:10]2[C:19]3[C:14](=[CH:15][N:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[N:12]([CH3:21])[C:11]=2[CH:22]=1.[H][H]>[Pd].CO.C(OCC)(=O)C>[CH:23]([C:8]1[C:7]([O:6][CH2:5][C@@H:4]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[CH2:3][CH:2]([CH3:1])[CH3:34])=[CH:22][C:11]2[N:12]([CH3:21])[C:13](=[O:20])[C:14]3[C:19]([C:10]=2[CH:9]=1)=[CH:18][CH:17]=[N:16][CH:15]=3)([CH3:25])[CH3:24]

Participants

6

Reactant 2

HCID 86710391HCID 86710391, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86710390HCID 86710390, compoundYield 1,146%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (S)-tert-butyl (4-methyl-1-((6-methyl-5-oxo-9-(prop-1-en-2-yl)-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)pentan-2-yl)carbamate (0.1 g, 0.215 mmol) and palladium on carbon (0.07 g, 0.066 mmol) in MeOH (3 mL) and ethyl acetate (3 mL) was stirred at RT under a balloon of hydrogen gas for 24 h. The reaction mixture was filtered through diatomaceous earth (Celite®) and the filtrate was concentrated under reduced pressure to afford (S)-tert-butyl (1-((9-isopropyl-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (0.04 g, 2.464 mmol, 1% yield) as a brown oil, which was carried on without further purification. LC/MS (ESI) m/e 468.4, [(M+H)+, calcd for C27H38N3O4, 468.3]; LC/MS retention time (method D): tR=1.00 min.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth (Celite®)
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2343454d3c1b46318d8850faa9631760
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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