1,4-Dioxane hydrochloride → (R)-5-Bromo-1-methyl-3-(5-(2-methylpiperazin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-one

HRID 1843177Notes

Reaction equation

HRID 1843177 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[N:16][C:17]([NH:20][C:21]3[C:22](=[O:29])[N:23]([CH3:28])[CH:24]=[C:25]([Br:27])[CH:26]=3)=[CH:18][CH:19]=2)[C@H:10]([CH3:30])[CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>CO>[Br:27][C:25]1[CH:26]=[C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]3[CH3:30])=[CH:15][N:16]=2)[C:22](=[O:29])[N:23]([CH3:28])[CH:24]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86683718(R)-tert-Butyl 4-(6-(5-Bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-3-yl)-3-methylpiperazine-1-carboxylate

Product 1

HCID 86683719(R)-5-Bromo-1-methyl-3-(5-(2-methylpiperazin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-oneYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 109c (600 mg, 1.26 mmol) in methanol (20 mL) was added HCl/dioxane (4.0 M, 4 mL). The reaction mixture was stirred at room temperature for 4 h. It was then concentrated at reduced pressure. The residue was basified with aqueous 1.0 M NaOH and extracted with DCM. The combined organic layer was washed with H2O and concentrated under reduced pressure to afford 109d (450 mg, 95%) as yellow solid. MS: [M+H]+ 378.

Workup

  1. concentrationIt was then concentrated at reduced pressure
  2. extractionextracted with DCM
  3. washThe combined organic layer was washed with H2O
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-88dbf0ec426e4a6db755f67144a0764d
Source dataset
uspto-grants-2015_02
Patent number
US08946213B2

Reaction notes

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