Dimethylamine, hydrochloride → 8-acetyl-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

HRID 572795Notes

Reaction equation

HRID 572795 reaction equation
[CH2:1]([N:3](C(C)C)[CH:4](C)C)C.[C:10]([C:13]1[CH:14]=[C:15]([C:30]([OH:32])=O)[CH:16]=[C:17]2[C:22]=1[O:21][C:20]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[CH:19][C:18]2=[O:29])(=[O:12])[CH3:11].Cl.CNC>C(Cl)Cl>[C:10]([C:13]1[CH:14]=[C:15]([C:30]([N:3]([CH3:4])[CH3:1])=[O:32])[CH:16]=[C:17]2[C:22]=1[O:21][C:20]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[CH:19][C:18]2=[O:29])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 582349818-acetyl-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

Product 1

HCID 582350348-acetyl-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamideYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-ethyl-N-isopropylpropan-2-amine (9.4 mL, 53.9 mmol) was added to 8-acetyl-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (5.7 g, 18 mmol) in DCM (100 mL). Five minutes later dimethylamine hydrochloride (2.9 g, 35.9 mmol) and 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate (6.92 g, 21.6 mmol) were added. The mixture was diluted with DCM, washed with NaHCO3, dried over magnesium sulfate and concentrated to afford the crude product which was purified by flash chromatography on silica gel eluting with 0 to 5% MeOH/DCM. The solvent was evaporated to dryness to afford 8-acetyl-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (2.75 g, 46%) as a yellow solid.

Workup

  1. washwashed with NaHCO3
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customto afford the crude product which
  5. customwas purified by flash chromatography on silica gel eluting with 0 to 5% MeOH/DCM
  6. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-3cb3a354b2ba4aa897b628bd7109fd13
Source dataset
uspto-grants-2015_05
Patent number
US09029374B2

Reaction notes

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