Hydrochloric Acid → 4-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-4-oxo-butanoic acid

HRID 710667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710667
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:17](=[O:35])[CH:18]([N:25]4[C:29]([CH3:30])=[CH:28][C:27]([C:31]([F:34])([F:33])[F:32])=[N:26]4)[CH2:19][C:20]([O:22]CC)=[O:21])[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.O[Li].O.C1COCC1.Cl>O.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:17](=[O:35])[CH:18]([N:25]4[C:29]([CH3:30])=[CH:28][C:27]([C:31]([F:32])([F:34])[F:33])=[N:26]4)[CH2:19][C:20]([OH:22])=[O:21])[C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86711682ethyl 4-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-4-oxo-butanoate

Produkt 1

HCID 867116834-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-4-oxo-butanoic acidAusbeute 103,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-4-oxo-butanoate (0.030 g, 0.060 mmol), LiOH.H2O (0.020 g, 0.47 mmol), THF (0.4 mL), MeOH (0.4 mL) and H2O (0.2 mL) was stirred for 30 min at rt. It was then acidified with 1 M aq. HCl (2 mL) and extracted with IPA/CHCl3 (1:2, 50 mL). The organic layer was separated, dried over Na2SO4, and concentrated in vacuo to yield 4-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-4-oxo-butanoic acid (0.029 g, 100%).

Aufarbeitung

  1. extractionextracted with IPA/CHCl3 (1:2, 50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0acadcd56f234ea887c866d1bc9c482c
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181241B2

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