Carbonate Ion → 3-(1-{[7-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinolin-8-yl]carbonyl}piperidin-4-yl)benzoic acid

HRID 69134

Reaktionsgleichung

Reaktionsgleichung von HRID 69134
[CH3:1][C:2]1[C:3]([C:22]([OH:24])=O)=[CH:4][C:5]2[C:6]3[N:15]([CH:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[N:14]=[CH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1.Cl.[NH:26]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=2)[C:35]([O:37]C)=[O:36])[CH2:28][CH2:27]1.ON1C2C=CC=CC=2N=N1.N=C=N.C(=O)([O-])[O-].[N-]=C=O>CN(C=O)C.C(N(CC)CC)C>[CH3:1][C:2]1[C:3]([C:22]([N:26]2[CH2:31][CH2:30][CH:29]([C:32]3[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=3)[C:35]([OH:37])=[O:36])[CH2:28][CH2:27]2)=[O:24])=[CH:4][C:5]2[C:6]3[N:15]([CH:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[N:14]=[CH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1

Komponenten

9

Edukt 6

HCID 19660Carbonate IonHCID 757711-HydroxybenzotriazoleHCID 105034IsocyanateHCID 160435CarbodiimideHCID 44607825Methyl 3-(piperidin-4-yl)benzoate hydrochlorideHCID 1363368547-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-8-carboxylic acid

Produkt 1

HCID 1363368633-(1-{[7-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinolin-8-yl]carbonyl}piperidin-4-yl)benzoic acidAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a mixture of 8.2 mg of 7-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-8-carboxylic acid, 7.7 mg of methyl 3-piperidin-4-yl-benzoate monohydrochloride, 3.4 mg of 1-hydroxybenzotriazole, 7.0 μL of triethylamine, and 1.0 mL of DMF was added 100 mg of PS-Carbodiimide (Biotage), followed by stirring at room temperature overnight. To the reaction mixture were added 75 mg of MP-Carbonate (Biotage), 50 mg of PS-Isocyanate (Biotage), and 0.5 mL of DMF at room temperature, followed by stirring for 2 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. To the obtained residue were added 0.5 mL of methanol, 0.5 mL of tetrahydrofuran, and 0.5 mL of a 1 M aqueous sodium hydroxide solution, followed by stirring at room temperature overnight. To the reaction mixture was added 0.5 mL of 1 M hydrochloric acid and the solvent was evaporated under reduced pressure. The obtained residue was purified by preparative HPLC (methanol/0.1% aqueous formic acid solution) to obtain 5.8 mg of 3-(1-{[7-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinolin-8-yl]carbonyl}piperidin-4-yl)benzoic acid.

Aufarbeitung

  1. stirringby stirring for 2 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo the obtained residue were added 0.5 mL of methanol, 0.5 mL of tetrahydrofuran, and 0.5 mL of a 1 M aqueous sodium hydroxide solution
  5. stirringby stirring at room temperature overnight
  6. additionTo the reaction mixture was added 0.5 mL of 1 M hydrochloric acid
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by preparative HPLC (methanol/0.1% aqueous formic acid solution)

Quellen und Nachweise

ORD-Eintrag
ord-550a46d6cb4e400e8ca14ebad9e37f34
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822448B2

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