HCID 131736068, compound → HCID 118598811, compound

HRID 1050375Notes

Reaction equation

HRID 1050375 reaction equation
[CH2:1]([N:8]([CH2:20][CH2:21][CH2:22][O:23][Si](C(C)(C)C)(C)C)[C:9]([C:11]1[NH:12][C:13](=[O:19])[C:14]([Br:18])=[CH:15][C:16]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1.Cl>[CH2:1]([N:8]([CH2:20][CH2:21][CH2:22][OH:23])[C:9]([C:11]1[NH:12][C:13](=[O:19])[C:14]([Br:18])=[CH:15][C:16]=1[CH3:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 131736068HCID 131736068, compound

Product 1

HCID 118598811HCID 118598811, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of N-benzyl-5-bromo-N-(3-((tert-butyldimethylsilyl)oxy) propyl)-3-methyl-6-oxo-1,6-dihydropyridine-2-carboxamide (3, 3.0 g, 6.0 mmol) in dioxane (20 mL), hydrogenchloride in dioxane (20 mL) was added at room temperature and the mixture was stirred for 16 h. After completion, the solvent was removed and the reaction was basified with aqueous sodium bicarbonate solution and extracted with 5% methanol/dichloromethane (3×200 mL). The organic layer was dried over sodium sulfate and solvent was removed under reduced pressure to get N-benzyl-5-bromo-N-(3-hydroxypropyl)-3-methyl-6-oxo-1,6-dihydropyridine-2-carboxamide (4) as brown liquid. Yield: 2.2 g, 95%; MS (ESI) m/z 381.22 [M−1]−.

Workup

  1. customAfter completion, the solvent was removed
  2. extractionextracted with 5% methanol/dichloromethane (3×200 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate and solvent
  4. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-0a95ff0c42844cf79dc9336403da94d4
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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