HCID 58574982, compound → HCID 58575224, compound

HRID 1189485Notes

Reaction equation

HRID 1189485 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-adde58dd904e4814be99311cf2c85158
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

Loading…