Water → 8-bromo-6-(morpholine-4-carbonyl)-2-morpholino-4H-chromen-4-one

HRID 41202Notes

Reaction equation

HRID 41202 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:19]([OH:21])=O)[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[CH:8][C:7]2=[O:18].CCN(C(C)C)C(C)C.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:19]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[O:21])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[CH:8][C:7]2=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 582350518-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

Product 1

HCID 866724148-bromo-6-(morpholine-4-carbonyl)-2-morpholino-4H-chromen-4-oneYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-propylphosphonic acid anhydride, cyclic trimer (50 wt % solution in EtAc) (8.57 ml, 14.68 mmol) was added at room temperature in one portion to a stirred solution of 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (2 g, 5.65 mmol), DIPEA (4.9 mL, 28.2 mmol) and morpholine (0.543 mL, 6.2 mmol) in DCM (14 mL). The mixture was stirred at room temperature for 1 h then water (1 mL) was then added. The reaction mixture was stirred for 15 mins and extracted with DCM. The combined organic layers were washed with water; the organic layer was washed with brine, dried over magnesium sulfate and concentrated to afford 8-bromo-6-(morpholine-4-carbonyl)-2-morpholino-4H-chromen-4-one (1.90 g, 79%) as a beige solid. Mass Spectrum: m/z [M+H]+=423.

Workup

  1. stirringThe reaction mixture was stirred for 15 mins
  2. extractionextracted with DCM
  3. washThe combined organic layers were washed with water
  4. washthe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-12a2b8aaa56949e2ada04c450bc5a99c
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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