HCID 131736068, compound → HCID 118598811, compound

HRID 1050410Notes

Reaction equation

HRID 1050410 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 (4, 3.0 g, 6.0 mmol) in dioxane (20 mL), hydrochloric acid in dioxane (20 mL) was added at room temperature. The mixture was stirred for 16 h. After completion, the solvent was removed. The residue was diluted with aqueous sodium bicarbonate and extracted with 5% methanol/dichloromethane (3×200 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to get N-benzyl-5-bromo-N-(3-hydroxypropyl)-3-methyl-6-oxo-1, 6-dihydropyridine-2-carboxamide (5) 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. additionThe residue was diluted with aqueous sodium bicarbonate
  3. extractionextracted with 5% methanol/dichloromethane (3×200 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bd0d12fdabfc42d0bbe0a34e059dd6bf
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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