4-(4-Chloro-phenyl)-4-[4-(3-methyl-1-trityl-1H-pyrazol-4-yl)-phenyl]-piperidine → HCID 178434522, Verbindung

HRID 924753Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924753
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([CH3:44])=[N:22][N:23](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:24]=4)=[CH:16][CH:15]=3)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>Cl.C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([CH3:44])=[N:22][NH:23][CH:24]=4)=[CH:16][CH:15]=3)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 1

HCID 672351344-(4-Chloro-phenyl)-4-[4-(3-methyl-1-trityl-1H-pyrazol-4-yl)-phenyl]-piperidine

Produkt 1

HCID 178434522HCID 178434522, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of 4-(4-chloro-phenyl)-4-[4-(3-methyl-1-trityl-1H-pyrazol-4-yl)-phenyl]-piperidine (178 mg, 0.30 mmol) in 5N hydrochloric acid (5 mL), THF (5 mL) and methanol (5 mL) was stirred for 140 minutes. The organic solvents were removed in vacuo then the resulting solution was diluted with 2N HCl and washed with ether. The aqueous phase was basified by addition of sodium hydroxide pellets then extracted with ethyl acetate. This organic extract was washed with brine, dried (MgSO4), filtered and concentrated to give a residue which was purified by column chromatography (SiO2), eluting with a gradient of 2M ammonia in methanol (5% to 7.5%) and dichloromethane. The product was further purified by preparative HPLC to give the title compound which was converted to its dihydrochloride salt (84 mg, 80%); LCMS (PS-A3) Rt 6.86 min [M+H]+ 352. 1H NMR (Me-d3-OD) δ 2.55 (3H, s), 2.70-2.75 (4H, m), 3.22-3.27 (4H, m), 7.35-7.41 (4H, m), 7.47-7.54 (4H, m), 8.32 (2H, s).

Aufarbeitung

  1. customThe organic solvents were removed in vacuo
  2. additionthe resulting solution was diluted with 2N HCl
  3. washwashed with ether
  4. additionThe aqueous phase was basified by addition of sodium hydroxide pellets
  5. extractionthen extracted with ethyl acetate
  6. extractionThis organic extract
  7. washwas washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a residue which
  12. customwas purified by column chromatography (SiO2)
  13. washeluting with a gradient of 2M ammonia in methanol (5% to 7.5%) and dichloromethane
  14. customThe product was further purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5331f55740f3488c90aa5709dab056c3
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283226B2

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