1,4-Dioxane hydrochloride → HCID 118021783, compound

HRID 575598Notes

Reaction equation

HRID 575598 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:10]([CH2:18][CH3:19])C(=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][CH2:18][CH3:19])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 118021567HCID 118021567, compound

Product 1

HCID 118021783HCID 118021783, 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-ethylcarbamate (99.0 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 for 30 min at 30° C. Then the mixture was filtered and the filter cake collected. The filtrate was adjusted to pH=9 with saturated aqueous NaHCO3, extracted with EA (20 mL), dried over Na2SO4, filtered and concentrated to give a light green solid which is combined with the filter cake to give the title compound (46.0 mg) which was carried forward without purification. 1H NMR (CDCl3 400 MHz): δ 6.72 (d, J=2.4 Hz, 1H), 6.20 (d, J=1.6 Hz, 1H), 3.51 (s, 3H), 3.09 (q, J=7.2 Hz, 2H), 1.27 (t, J=7.2 Hz, 3H). LCMS (M+H)+ 231.

Workup

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

Sources & evidence

ORD record
ord-f373a3979d034c7f855fe2a76246169e
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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