4-Methylmorpholine → N-{4-[(2-methylpropyl)amino]quinolin-3-yl}-3-(2-methyl-1,3-dioxolan-2-yl)propanamide

HRID 599452Notes

Reaction equation

HRID 599452 reaction equation
[CH3:1][CH:2]([CH3:16])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[NH2:15].[CH3:17][C:18]1([CH2:23][CH2:24][C:25](O)=[O:26])[O:22][CH2:21][CH2:20][O:19]1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.C(=O)(O)[O-].[Na+]>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH3:1][CH:2]([CH3:16])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[NH:15][C:25](=[O:26])[CH2:24][CH2:23][C:18]1([CH3:17])[O:22][CH2:21][CH2:20][O:19]1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109317243-(2-methyl-1,3-dioxolan-2-yl)propanoic AcidHCID 11298872N4-(2-methylpropyl)quinoline-3,4-diamine

Product 1

HCID 67052427N-{4-[(2-methylpropyl)amino]quinolin-3-yl}-3-(2-methyl-1,3-dioxolan-2-yl)propanamideYield 71.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a cooled solution of N4-(2-methylpropyl)quinoline-3,4-diamine (2.15 g, 10 mmol) in DMF (40 mL) was added 3-(2-methyl-1,3-dioxolan-2-yl)propanoic acid (2.40 g, 15 mmol), followed by 4-methylmorpholine (1.6 mL, 15 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (2.9 g, 15 mmol). The resulting suspension was stirred at room temperature and 4-dimethylaminopyridine (0.12 g, 1 mmol) was added. The dark yellow solution was stirred at room temperature for 16 hours, then saturated aqueous sodium bicarbonate (100 mL) was added. The mixture was transferred to a separatory funnel and was extracted with dichloromethane (2×100 mL). The organic layers were combined, washed with saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford an oil that was purified by flash chromatography (silica gel, elution with 5% methanol in dichloromethane) to provide 2.55 g of N-{4-[(2-methylpropyl)amino]quinolin-3-yl}-3-(2-methyl-1,3-dioxolan-2-yl)propanamide.

Workup

  1. stirringThe dark yellow solution was stirred at room temperature for 16 hours
  2. customThe mixture was transferred to a separatory funnel
  3. extractionwas extracted with dichloromethane (2×100 mL)
  4. washwashed with saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford an oil that
  9. customwas purified by flash chromatography (silica gel, elution with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e9a278939dcc4c329f7db3e1e0e77d92
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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