HCID 86663350, compound → HCID 66798054, compound

HRID 1397535Notes

Reaction equation

HRID 1397535 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)[N:5]=[C:4]([NH:18][C@H:19]2[C@@H:23]3[O:24][C:25]([CH3:28])([CH3:27])[O:26][C@@H:22]3[C@@H:21]([CH2:29][OH:30])[CH2:20]2)[N:3]=1>CCO.[Pd]>[C@@H:9]1([NH:8][C:6]2[N:7]=[CH:2][N:3]=[C:4]([NH:18][C@H:19]3[C@@H:23]4[O:24][C:25]([CH3:27])([CH3:28])[O:26][C@@H:22]4[C@@H:21]([CH2:29][OH:30])[CH2:20]3)[N:5]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 86663350HCID 86663350, compound

Product 1

HCID 66798054HCID 66798054, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of [(3aR,4R,6R,6aS)-6-({4-Chloro-6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-1,3,5-triazin-2-yl}amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methanol (182 mg, 0.421 mmol) in EtOH (2.91 mL) was added 10% palladium on carbon (44.8 mg) and the mixture was placed under an atmosphere of hydrogen for 2 d. Filtration of the mixture through a pad of celite, followed by silica gel chromatography eluting with 5% MeOH in DCM afforded the title compound as a white solid (80.0 mg, 48%). LC/MS: Rt=1.24 min, ES+ 398 (FA standard).

Workup

  1. filtrationFiltration of the mixture through a pad of celite
  2. washeluting with 5% MeOH in DCM

Sources & evidence

ORD record
ord-f6d599664fd24e7799a23683229c0a10
Source dataset
uspto-grants-2014_12
Patent number
US08901136B2

Reaction notes

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