Hydrochloric Acid → 6-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)pyridazine-3-carboxylic acid

HRID 1714864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1714864
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[N:16][C:15]([C:18]([O:20]C)=[O:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.O.[OH-].[Li+].Cl>C1COCC1.O>[F:26][C:2]([F:1])([F:27])[C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[N:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68505610Methyl 6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carboxylate

Produkt 1

HCID 462254266-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)pyridazine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of methyl 6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carboxylate (800 mg, 2.1 mmol) and lithium hydroxide monohydrate (352 mg, 8.4 mmol) in THF (10 mL) and water (5 mL) was stirred at r.t. overnight, then acidified with 1M aqueous HCl (9 mL). Volatile materials were removed in vacuo. The residue was diluted with water and extracted with EtOAc. The organic extract was washed with diluted brine, dried (Na2SO4), concentrated and swished with Et2O to give the title compound as a white powder. 1H NMR (400 MHz, acetone-d6): δ 1.97 (m, 2H), 2.15-2.21 (m, 2H), 4.00-4.10 (m, 4H), 5.04-5.08 (m, 1H), 7.13 (t, 1H), 7.39 (m, 2H), 7.63-7.69 (m, 2H), 7.94 (d, 1H).

Aufarbeitung

  1. customVolatile materials were removed in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed with diluted brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a0181077ca404f4f8125e1c489677742
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799787B2

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