HCID 57722465, compound → HCID 57722467, compound

HRID 220070Notes

Reaction equation

HRID 220070 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-b9387ef933104a21977b7975d17fd165
Source dataset
uspto-grants-2012_06
Patent number
US08202864B2

Reaction notes

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