Dimethylamine → HCID 86682951, compound

HRID 1497090Notes

Reaction equation

HRID 1497090 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](OS(C(F)(F)F)(=O)=O)=[N:8][C:9]2[C:14]([C:15]=1[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])=[CH:13][C:12]([Cl:24])=[CH:11][CH:10]=2)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:39][NH:40][CH3:41]>C1COCC1.O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([N:40]([CH3:41])[CH3:39])=[N:8][C:9]2[C:14]([C:15]=1[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])=[CH:13][C:12]([Cl:24])=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 86682952HCID 86682952, compound

Product 1

HCID 86682951HCID 86682951, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-chloro-4-(2-chloro-benzyl)-2-trifluoromethanesulfonyloxy-quinoline-3-carboxylic acid ethyl ester (100 mg, 0.2 mmol) in THF (2 ml) was added potassium carbonate (109 mg, 0.79 mmol) and dimethylamine (2M solution in THF; 0.5 ml, 0.98 mmol) at 25° C. and the resulting reaction mixture was stirred at 70° C. for 3 h. The mixture was diluted with water (5 ml), and extracted with EtOAc (3×15 ml) and the organic phases were combined and washed with brine (15 ml), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography (3% EtOAc/hexane) to give 6-chloro-4-(2-chloro-benzyl)-2-dimethylamino-quinoline-3-carboxylic acid ethyl ester (55 mg, 69%) as pale yellow solid. LC-MS (ESI): 403 (M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with EtOAc (3×15 ml)
  3. washwashed with brine (15 ml)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by column chromatography (3% EtOAc/hexane)

Sources & evidence

ORD record
ord-b2b9f14815ca45cfbff4000860daa0cc
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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