HCID 57722465, compound → HCID 57722467, compound

HRID 402852Notes

Reaction equation

HRID 402852 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C@H:10]1[NH:15][C:14](=[O:16])[C@@H:13]([C@@H:17]([CH3:20])[CH2:18][CH3:19])[N:12]([CH:21]([C:39]2[CH:40]=[N:41][C:42]([CH3:46])=[CH:43][C:44]=2[CH3:45])[C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31]CC2C=CC=CC=2)=[O:23])[C:11]1=[O:47]>C(O)C.[Pd]>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C@H:10]1[NH:15][C:14](=[O:16])[C@@H:13]([C@@H:17]([CH3:20])[CH2:18][CH3:19])[N:12]([CH:21]([C:39]2[CH:40]=[N:41][C:42]([CH3:46])=[CH:43][C:44]=2[CH3:45])[C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[OH:31])=[O:23])[C:11]1=[O:47]

Participants

4

Reactant 1

HCID 57722465HCID 57722465, compound2×

Product 1

HCID 57722467HCID 57722467, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-{(3R,6R)-3-(2,3-Dihydro-1H-inden-2-yl)-6-[(1S)-1-methylpropyl]-2,5-dioxo-1-piperazinyl}-2-(4,6-dimethyl-3-pyridinyl)-N-{2-[(phenylmethyl)oxy]phenyl}acetamide (intermediate 3) (3.30 g) was dissolved in ethanol (75 ml) and hydrogenated over palladium on charcoal (wet 10% Pd, 0.50 g) for 20 hours. The catalyst was removed by filtration and washed with dichloromethane. The combined filtrate and washings were evaporated in vacuo. The residue was applied to a 90 g Biotage column and eluted with ethyl acetate. The required fractions were combined and evaporated in vacuo to give 2-{(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-6-[(1S)-1-methylpropyl]-2,5-dioxo-1-piperazinyl}-2-(4,6-dimethyl-3-pyridinyl)-N-(2-hydroxyphenyl)acetamide (2.43 g, 87%) as a pale yellow solid.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with dichloromethane
  3. customThe combined filtrate and washings were evaporated in vacuo
  4. washeluted with ethyl acetate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-de94ebc85f2446fa9a655366fa677470
Source dataset
uspto-grants-2014_06
Patent number
US08742099B2

Reaction notes

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