1-Aminocyclopropane-1-carboxylic acid → 1-[3-(6-Cyano-4,4,8-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamino]-cyclopropanecarboxylic acid

HRID 1036869

Reaktionsgleichung

Reaktionsgleichung von HRID 1036869
Br[C:2]1[CH:3]=[C:4]([CH:8]2[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]3[C:10](=[C:11]([CH3:22])[CH:12]=[C:13]([C:20]#[N:21])[CH:14]=3)[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[NH2:23][C:24]1([C:27]([OH:29])=[O:28])[CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[C:20]([C:13]1[CH:14]=[C:15]2[C:10](=[C:11]([CH3:22])[CH:12]=1)[NH:9][CH:8]([C:4]1[CH:3]=[C:2]([NH:23][C:24]3([C:27]([OH:29])=[O:28])[CH2:26][CH2:25]3)[CH:7]=[CH:6][CH:5]=1)[CH2:17][C:16]2([CH3:19])[CH3:18])#[N:21]

Komponenten

6

Edukt 3

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 11430Potassium CarbonateHCID 672899872-(3-Bromophenyl)-4,4,8-trimethyl-1,2,3,4-tetrahydroquinoline-6-carbonitrile

Produkt 1

HCID 569666421-[3-(6-Cyano-4,4,8-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamino]-cyclopropanecarboxylic acidAusbeute 21,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of 2-(3-bromo-phenyl)-4,4,8-trimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonitrile (355.0 mg, 1.0 mmol), copper(I) iodide (57.0 mg, 0.3 mmol), 1-amino-cyclopropanecarboxylic acid (309.0 mg, 3.0 mmol) and potassium carbonate (415.0 mg, 3.0 mmol) in dimethyl sulfoxide (2.0 mL) was stirred at 120° C. for 16 h. Then the reaction mixture was cooled to room temperature and extracted with ethyl acetate (150 mL×2), washed with water (50 mL×2) and saturated aqueous ammonium chloride solution (50 mL×2), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 1-[3-(6-cyano-4,4,8-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamino]-cyclopropanecarboxylic acid (79.8 mg, 21.3%) as a white solid: LC/MS m/e obsd. (ESI+) [(M+H)+] 376.2.

Aufarbeitung

  1. extractionextracted with ethyl acetate (150 mL×2)
  2. washwashed with water (50 mL×2) and saturated aqueous ammonium chloride solution (50 mL×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water)

Quellen und Nachweise

ORD-Eintrag
ord-8eb67cb5b2c145bd817725978a771493
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546427B2

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