1,4-Dioxane hydrochloride → HCID 101043627, compound

HRID 518326Notes

Reaction equation

HRID 518326 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:10](C)[C:11](=O)OC(C)(C)C)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.Cl.O1CCOCC1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][CH3:11])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 118022858HCID 118022858, compound

Product 1

HCID 101043627HCID 101043627, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of tert-butyl N-(5-bromo-1-methyl-2-oxopyridin-3-yl)-N-methylcarbamate (94.8 mg, crude) in DCM (10 mL) was added HCl/dioxane (1 mL, 4 M) dropwise with stirring at 30° C. The reaction mixture was stirred at 30° C. for 30 min. The mixture was filtered and the filter cake collected. The filtrate was adjusted to pH=9 with saturated aqueous NaHCO3, extracted with ethyl acetate (20 mL), dried over Na2SO4, filtered and concentrated to give a green solid which was combined with the filter cake to give the title compound (43.2 mg). 1H NMR (CDCl3 400 MHz): δ 6.74 (d, J=2.4 Hz, 1H), 6.18 (d, J=2.4 Hz, 1H), 5.15 (s, 1H), 3.53 (s, 3H), 2.83 (s, 3H). LCMS (M+H)+ 217

Workup

  1. stirringThe reaction mixture was stirred at 30° C. for 30 min
  2. filtrationThe mixture was filtered
  3. customthe filter cake collected
  4. extractionextracted with ethyl acetate (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a green solid which

Sources & evidence

ORD record
ord-5b088f0700bb4f7dbf2a8fa5ae8c2fbe
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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