(2-Bromoethoxy)-tert-butyldimethylsilane → 5-Bromo-3-(5-(4-(2-(tert-butyldimethylsilyloxy)ethyl)piperazin-1-yl)pyridine-2-ylamino)-1-methylpyridin-2(1H)-one

HRID 1021673Notes

Reaction equation

HRID 1021673 reaction equation
Br[CH2:2][CH2:3][O:4][Si:5]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].[Br:12][C:13]1[CH:14]=[C:15]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[CH:24][N:23]=2)[C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1>CC#N>[Br:12][C:13]1[CH:14]=[C:15]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][O:4][Si:5]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6])[CH2:30][CH2:29]3)=[CH:24][N:23]=2)[C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1

Participants

4

Reactant 2

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 580436655-Bromo-1-methyl-3-((5-(piperazin-1-yl)-pyridin-2-yl)amino)pyridin-2(1H)-one

Product 1

HCID 866842165-Bromo-3-(5-(4-(2-(tert-butyldimethylsilyloxy)ethyl)piperazin-1-yl)pyridine-2-ylamino)-1-methylpyridin-2(1H)-oneYield 90.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 123a (231 mg, 0.96 mmol) in MeCN (40 mL) at 70° C. was added 5-bromo-1-methyl-3-(5-(piperazin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-one 101j (350 mg, 0.96 mmol). The reaction mixture was stirred for 3 days. It was then filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (30:1) to afford 123b as yellow solid (452 mg, 90%). MS: [M+H]+ 524.7.

Workup

  1. filtrationIt was then filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica-gel column chromatography
  4. washeluting with dichloromethane/methanol (30:1)

Sources & evidence

ORD record
ord-3a10b4c5560a4db881437e6e4bb4be45
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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