Trifluoroacetic acid → (R)-5-bromo-1-methyl-3-(5-(3-methylpiperazin-1-yl)pyridin-2-ylamino)pyridine-2(1H)-one

HRID 1026414Notes

Reaction equation

HRID 1026414 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[C@H:19]([CH3:30])[CH2:18]3)=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH2:22][CH2:21][NH:20][C@H:19]([CH3:30])[CH2:18]3)=[CH:15][N:16]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86683712(R)-tert-Butyl 4-(6-(5-Bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino) pyridine-3-yl)-2-methylpiperazine-1-carboxylate

Product 1

HCID 86683713(R)-5-bromo-1-methyl-3-(5-(3-methylpiperazin-1-yl)pyridin-2-ylamino)pyridine-2(1H)-oneYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 108c (624 mg, 1.3 mmol) in dichloromethane (8 mL) was added trifluoroacetic acid dropwise (300 mg, 2.6 mmol) at room temperature. Then the mixture was stirred for overnight. 2.0 N NaOH was added to adjust pH to greater than 10. Then the mixture was extracted with ethyl acetate (50 mL×2). The combined organic layer was washed with brine (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 108d as a brown solid (300 mg, 61%). LCMS: [M+H]+ 380

Workup

  1. extractionThen the mixture was extracted with ethyl acetate (50 mL×2)
  2. washThe combined organic layer was washed with brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aabf701ddb894daeaf1a4502b43afb95
Source dataset
uspto-grants-2014_05
Patent number
US08729072B2

Reaction notes

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