HCID 57722465, compound → HCID 57722467, compound

HRID 1479277Notes

Reaction equation

HRID 1479277 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-f0edeb58e549433a94ccc6b74f2e606e
Source dataset
uspto-grants-2016_08
Patent number
US09408851B2

Reaction notes

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