Hydrochloric Acid → HCID 58235000, compound

HRID 41215Notes

Reaction equation

HRID 41215 reaction equation
CCN(C(C)C)C(C)C.[Br:10][C:11]1[CH:12]=[C:13]([C:27]([O:29][CH3:30])=[O:28])[CH:14]=[C:15]2[C:20]=1[O:19][C:18](S(CC)(=O)=O)=[CH:17][C:16]2=[O:26].Cl.[CH3:32][C@H:33]1[O:38][CH2:37][CH2:36][NH:35][CH2:34]1.Cl>C(Cl)Cl.O>[Br:10][C:11]1[CH:12]=[C:13]([C:27]([O:29][CH3:30])=[O:28])[CH:14]=[C:15]2[C:20]=1[O:19][C:18]([N:35]1[CH2:36][CH2:37][O:38][C@H:33]([CH3:32])[CH2:34]1)=[CH:17][C:16]2=[O:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 42609645(2R)-2-Methylmorpholine hydrochlorideHCID 58235035methyl 8-bromo-2-(ethylsulfonyl)-4-oxo-4H-chromene-6-carboxylate

Product 1

HCID 58235000HCID 58235000, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

DIPEA (51.7 mL, 296.91 mmol) was added dropwise to a stirred solution of methyl 8-bromo-2-(ethylsulfonyl)-4-oxo-4H-chromene-6-carboxylate (44.56 g, 118.77 mmol) and (R)-2-methylmorpholine hydrochloride (22.88 g, 166.27 mmol) in DCM (430 mL) at 5° C. under nitrogen. The resulting suspension was stirred at room temperature for 1 h. The reaction mixture was diluted with water and quenched slowly with HCl 1M (119 mL, 118.77 mmol) (pH 7). The phases were separated and the organic phase was washed with water, brine, dried over MgSO4 and concentrated. The crude product was triturated in EtAc for 1 h, the solid was collected by filtration and dried to afford methyl 8-bromo-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate (32.6 g, 67%) as a white solid. Mass Spectrum: m/z [M+H]+=384.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was triturated in EtAc for 1 h
  6. filtrationthe solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-4924f2d6c35d4067a2ecd2984f927ae9
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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