Diisopropylethylamine → 8-bromo-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

HRID 41207Notes

Reaction equation

HRID 41207 reaction equation
[B-](F)(F)(F)F.[CH3:6][N:7](C(ON1C(=O)CCC1=O)=[N+](C)C)[CH3:8].[Br:21][C:22]1[CH:23]=[C:24]([C:39]([OH:41])=O)[CH:25]=[C:26]2[C:31]=1[O:30][C:29]([N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1)=[CH:28][C:27]2=[O:38].CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:21][C:22]1[CH:23]=[C:24]([C:39]([N:7]([CH3:8])[CH3:6])=[O:41])[CH:25]=[C:26]2[C:31]=1[O:30][C:29]([N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1)=[CH:28][C:27]2=[O:38]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate2×HCID 582350518-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

Product 1

HCID 582350908-bromo-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamideYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TSTU (6.55 g, 21.74 mmol) was added to a stirred solution of 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (7 g, 19.77 mmol) and DIPEA (3.79 mL, 21.74 mmol) dissolved in DCM (100 mL) under nitrogen. The resulting suspension was stirred at room temperature for 4 h. More TSTU (6.55 g, 21.74 mmol) and DIPEA (3.79 mL, 21.74 mmol) were added and stirring was pursued for a further 16 h. The reaction mixture was quenched with a saturated aqueous solution of sodium hydrogencarbonate and extracted with DCM and a little MeOH. The combined organic phases were dried over MgSO4, concentrated and purified by flash chromatography on silica gel eluting with 3 to 5% MeOH in DCM. The solvent was evaporated to dryness to afford 8-bromo-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (7.70 g, 102%) as a beige solid. Mass Spectrum: m/z [M+H]+=381.

Workup

  1. stirringstirring
  2. waitwas pursued for a further 16 h
  3. customThe reaction mixture was quenched with a saturated aqueous solution of sodium hydrogencarbonate
  4. extractionextracted with DCM
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. concentrationconcentrated
  7. custompurified by flash chromatography on silica gel eluting with 3 to 5% MeOH in DCM
  8. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-c64ab93de0bd42e1a77aba30341b1cdd
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

Loading…