HCID 58574982, compound → HCID 58575224, compound

HRID 1807873Notes

Reaction equation

HRID 1807873 reaction equation
C([O:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[N:18]2[C:19]3[C:24]([NH:25][C:26](=[O:27])[C:17]2=[N:16][N:15]=1)=[CH:23][C:22]([C:28]([N:30]1[CH2:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31]1)=[O:29])=[C:21]([CH3:39])[CH:20]=3)C1C=CC=CC=1>[Pd].C(O)C>[CH2:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:38][N:30]1[C:28]([C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[CH3:39])[N:18]1[C:14]([C@@H:10]3[CH2:11][CH2:12][CH2:13][C@@H:9]3[OH:8])=[N:15][N:16]=[C:17]1[C:26](=[O:27])[NH:25]2)=[O:29]

Participants

4

Reactant 1

HCID 58574982HCID 58574982, compound

Product 1

HCID 58575224HCID 58575224, compoundYield 38.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 0.355 g of 1-[cis-2-(benzyloxy)cyclopentyl]-7-(1,3-dihydro-2H-isoindol-2-ylcarbonyl)-8-methyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one and 50.0 mL of ethanol was added 142 mg of 10% palladium on carbon (50% wet), followed by stirring overnight under a hydrogen atmosphere. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=97/3 to 90/10) to give a powder from 2-propanol, thereby obtaining 114 mg of 7-(1,3-dihydro-2H-isoindol-2-ylcarbonyl)-1-[cis-2-hydroxycyclopentyl]-8-methyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one as a colorless solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=97/3 to 90/10)
  4. customto give a powder from 2-propanol

Sources & evidence

ORD record
ord-374460121dc64d62a00d5431691c0ad3
Source dataset
uspto-grants-2013_01
Patent number
US08357688B2

Reaction notes

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