Potassium Carbonate → HCID 70979925, compound

HRID 572357Notes

Reaction equation

HRID 572357 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]([OH:20])=[O:19])=[CH:16][N:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][N:25]=2)[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:40][CH2:41][N:42]([CH3:44])[CH3:43]>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][CH2:40][CH2:41][N:42]([CH3:44])[CH3:43])=[O:19])=[CH:16][N:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][N:25]=2)[CH2:6][C@H:5]1[CH3:32])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 178642-BromoethyldimethylamineHCID 70979776HCID 70979776, compound

Product 1

HCID 70979925HCID 70979925, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)nicotinic acid (for a preparation see Intermediate 7) (54 mg, 0.126 mmol) in DMF (5 mL) were added K2CO3 (26.2 mg, 0.189 mmol) and 2-bromo-N,N-dimethylethanamine (28.8 mg, 0.189 mmol). The resulting mixture was stirred at room temperature for 3 h, the reaction mixture was concentrated under reduced pressure and 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 6-((2R,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)nicotinate (16.5 mg, 24%) as a viscous colourless oil. LCMS (Formate, 2 min), Rt=0.69 min, MH+=499.

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-553258c1441242b39c2f53c03725f02f
Source dataset
uspto-grants-2015_05
Patent number
US09029395B2

Reaction notes

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