HCID 86663352, compound → HCID 66797874, compound

HRID 1747621Notes

Reaction equation

HRID 1747621 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:13][C@@H:12]([NH:14][C:15]2[N:20]=[C:19](Cl)[N:18]=[C:17]([NH:22][C@H:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]([CH3:33])([CH3:32])[CH2:24]3)[N:16]=2)[CH2:11][C@@H:10]1[CH2:34][OH:35])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CCO.[Pd].[OH-].[OH-].[Pd+2]>[Si:1]([O:8][C@H:9]1[CH2:13][C@H:12]([NH:14][C:15]2[N:16]=[C:17]([NH:22][C@@H:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]([CH3:33])([CH3:32])[CH2:24]3)[N:18]=[CH:19][N:20]=2)[CH2:11][C@H:10]1[CH2:34][OH:35])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 86663352HCID 86663352, compound

Product 1

HCID 66797874HCID 66797874, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of {(1R,2R,4S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-[(4-chloro-6-{[(1R)-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl]amino}-1,3,5-triazin-2-yl)amino]cyclopentyl}-methanol (0.083 g, 0.16 mmol) in EtOH (1.11 mL) was added Pd (10% on carbon) (0.0170 g, 0.0160 mmol) and the mixture was stirred under an atmosphere of hydrogen for 4 d. The reaction was purged with nitrogen for 30 minutes then Pd(OH)2 (20% on carbon dry weight) (0.022 g, 0.016 mmol) was added and the mixture was stirred for 4 h under an atmosphere of hydrogen. Filtration of the mixture through a pad of celite, followed by flash chromatography (50-100% EtOAc/hexanes) afforded the title compound (0.027 g, 35%). LC/MS: Rt=1.81 min, ES+ 484 (FA standard).

Workup

  1. customThe reaction was purged with nitrogen for 30 minutes
  2. stirringthe mixture was stirred for 4 h under an atmosphere of hydrogen
  3. filtrationFiltration of the mixture through a pad of celite

Sources & evidence

ORD record
ord-a6dde8ad044340ffb7acd7635be4815b
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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