Hydrochloric Acid → 8-(1-aminoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

HRID 572797Notes

Reaction equation

HRID 572797 reaction equation
Cl.CC(C)([S@]([NH:7][CH:8]([C:10]1[CH:11]=[C:12]([C:27]([N:29]([CH3:31])[CH3:30])=[O:28])[CH:13]=[C:14]2[C:19]=1[O:18][C:17]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[CH:16][C:15]2=[O:26])[CH3:9])=O)C>O1CCOCC1>[NH2:7][CH:8]([C:10]1[CH:11]=[C:12]([C:27]([N:29]([CH3:30])[CH3:31])=[O:28])[CH:13]=[C:14]2[C:19]=1[O:18][C:17]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[CH:16][C:15]2=[O:26])[CH3:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 582350578-(1-((R)-1,1-dimethylethyl sulfinamido)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

Product 1

HCID 582349768-(1-aminoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamideYield 89.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Hydrogen chloride in dioxane 4M (15 mL, 60.1 mmol) was added to 8-(1-((R)-1,1-dimethylethylsulfinamido)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (2.7 g, 6.0 mmol) dissolved in dioxane (40 mL). The resulting white suspension was stirred at RT for 1 hour, collected by filtration, washed with diethyl ether and dried. It was dissolved into a 5% methanolic ammonia (7 N) sol. in DCM (200 mL) and stirred for 5 minutes. The precipitate (NH4Cl) was removed by filtration and the filtrate was concentrated to dryness to afford 8-(1-aminoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (single enantiomer, 1.85 g, 89%) as an off-white solid. Mass Spectrum: M+H+ 346. [α]D20°: +35° in acetonitrile.

Workup

  1. filtrationcollected by filtration
  2. washwashed with diethyl ether
  3. customdried
  4. dissolutionIt was dissolved into a 5% methanolic ammonia (7 N) sol. in DCM (200 mL)
  5. stirringstirred for 5 minutes
  6. customThe precipitate (NH4Cl) was removed by filtration
  7. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-77dfece841c5451fab2e06943545257e
Source dataset
uspto-grants-2015_05
Patent number
US09029374B2

Reaction notes

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