Potassium Carbonate → 2-(dimethylamino)ethyl 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

HRID 572359Notes

Reaction equation

HRID 572359 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([O-:20])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25])[CH2:6][C@@H:5]1[CH3:30])(=[O:3])[CH3:2].[Li+].Br[CH2:33][CH2:34][N:35]([CH3:37])[CH3:36].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([O:20][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25])[CH2:6][C@@H:5]1[CH3:30])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 178642-BromoethyldimethylamineHCID 70976581HCID 70976581, compound

Product 1

HCID 714648592-(dimethylamino)ethyl 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoateYield 5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of lithium 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (for a preparation see Intermediate 20) (246 mg, 0.591 mmol) and 2-bromo-N,N-dimethylethanamine (135 mg, 0.886 mmol) in DMF (5 mL) was added potassium carbonate (122 mg, 0.886 mmol). The resulting mixture was stirred at room temperature for 2 h, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in a 1:1 MeOH/DMSO mixture and purified by MDAP (formate). The appropriate fractions were combined and concentrated in vacuo to give 2-(dimethylamino)ethyl 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (14.5 mg, 5%) as a viscous colourless oil. LCMS (Formate, 2 min), Rt=0.72 min, MH+=482.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in a 1:1 MeOH/DMSO mixture
  3. custompurified by MDAP (formate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b584174bb45430f9aa83857c9bc868a
Source dataset
uspto-grants-2015_05
Patent number
US09029395B2

Reaction notes

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