Diethylamine → HCID 86683007, compound

HRID 1497173Notes

Reaction equation

HRID 1497173 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[C:6]([O:10][C:11]([C:13]1[C:14](OS(C(F)(F)F)(=O)=O)=[N:15][C:16]2[C:21]([C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]([CH3:31])[CH3:30])[CH:24]=1)=[CH:20][C:19]([Cl:32])=[CH:18][CH:17]=2)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[C:6]([O:10][C:11]([C:13]1[C:14]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[N:15][C:16]2[C:21]([C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]([CH3:30])[CH3:31])[CH:24]=1)=[CH:20][C:19]([Cl:32])=[CH:18][CH:17]=2)=[O:12])([CH3:7])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 86683008HCID 86683008, compound

Product 1

HCID 86683007HCID 86683007, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of diethyl amine (0.078 ml, 0.75 mmol) in THF (5 ml) was added 6-chloro-4-(3-isopropyl-phenyl)-2-trifluoromethanesulfonyloxy-quinoline-3-carboxylic acid tert-butyl ester (200 mg, 0.38 mmol) and potassium carbonate (208 mg, 1.51 mmol) at 25° C. The resulting reaction mixture was stirred at 70° C. for 3 h. Volatiles were removed in vacuo and the resulting crude mixture was diluted with water (15 ml), and extracted with EtOAc (2×30 ml). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (3% EtOAc in hexane) to afford 6-chloro-2-diethylamino-4-(3-isopropyl-phenyl)-quinoline-3-carboxylic acid tert-butyl ester (110 mg, 64%) as a pale yellow solid. LC-MS (ESI): 453 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. customVolatiles were removed in vacuo
  3. additionthe resulting crude mixture was diluted with water (15 ml)
  4. extractionextracted with EtOAc (2×30 ml)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a crude residue which
  9. customwas purified by flash column chromatography (3% EtOAc in hexane)

Sources & evidence

ORD record
ord-2fc1e1cca1144a06a94469aac2e0cdb4
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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