Hydrochloric Acid → 1-{4-[3-(ethoxycarbonyl)-1-(4-methoxyphenyl)-7-oxo-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl]phenyl}cyclopropanecarboxylic acid

HRID 971137Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 971137
I[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]2[CH2:14]C2)[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:27]3[C:28](=[O:32])[NH:29][CH2:30][CH2:31][C:26]=3[C:25]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[N:24]2)=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.Cl>CS(C)=O.[Cu]I.CCOC(C)=O>[CH2:36]([O:35][C:33]([C:25]1[C:26]2[CH2:31][CH2:30][N:29]([C:2]3[CH:3]=[CH:4][C:5]([C:8]4([C:9]([OH:11])=[O:10])[CH2:12][CH2:14]4)=[CH:6][CH:7]=3)[C:28](=[O:32])[C:27]=2[N:23]([C:20]2[CH:19]=[CH:18][C:17]([O:16][CH3:15])=[CH:22][CH:21]=2)[N:24]=1)=[O:34])[CH3:37]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 22240468Ethyl 1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxylateHCID 695169744-Iodophenylcyclopropyl acetic acid

Produkt 1

HCID 695164601-{4-[3-(ethoxycarbonyl)-1-(4-methoxyphenyl)-7-oxo-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl]phenyl}cyclopropanecarboxylic acidAusbeute 72,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Part A. 4-Iodophenylcyclopropyl acetic acid (1.93 g, 6.70 mmol) and 1-(4-methoxyphenyl)-3-(ethoxycarbonyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one (1.41 g, 4.46 mmol) were stirred in DMSO (4 mL) under N2. K2CO3 (1.84 g, 13.33 mmol, 3.0 eq) was added followed by the addition of 1,10-phenanthroline (0.15 g, 20 mol %) and CuI (0.16 g, 20 mol %). The resulting mixture was stirred at 110° C. overnight. LC-MS showed completion of the reaction. EtOAc was added to the cooled solution. It was acidified with 1N HCl, and the organic layer was washed with H2O, and brine, dried over MgSO4, filtered, and concentrated to afford 1-{4-[3-(ethoxycarbonyl)-1-(4-methoxyphenyl)-7-oxo-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl]phenyl}cyclopropanecarboxylic acid (1.54 g, yield: 72.6%). LC/MS (ESI+) 476.4 (M+H)+, tR=2.58 min (10–90% CH3CN/H2O in a 4-min run).

Aufarbeitung

  1. customcompletion of the reaction
  2. washthe organic layer was washed with H2O, and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c25e834455b14700a0e4141103f0d2e8
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312214B2

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