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Hydrochloric Acid → 1-[6-(5-{1-[4-(Methylsulfonyl)phenyl]-2-(tetrahydro-2h-pyran-4-yl)ethyl}-1h-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol

HRID 1882006
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1882006
CC1(C)[O:6][CH:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13](=O)[CH2:14][CH2:15][C:16](=O)[CH:17]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=3)[CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:11][CH:12]=2)[CH2:4][O:3]1.C([O-])(=O)C.[NH4+:42].Cl>C(O)(=O)C.C(OCC)(=O)C.O1CCCC1>[CH3:34][S:31]([C:28]1[CH:27]=[CH:26][C:25]([CH:17]([C:16]2[NH:42][C:13]([C:10]3[N:11]=[CH:12][C:7]([CH:5]([OH:6])[CH2:4][OH:3])=[CH:8][CH:9]=3)=[CH:14][CH:15]=2)[CH2:18][CH:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[CH:30][CH:29]=1)(=[O:33])=[O:32]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 593315341-[5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-2-yl]-5-[4-(methylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

Produkt 1

HCID 593314071-[6-(5-{1-[4-(Methylsulfonyl)phenyl]-2-(tetrahydro-2h-pyran-4-yl)ethyl}-1h-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diolAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 1-[5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-2-yl]-5-[4-(methylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (232 mg) in acetic acid (5 mL) was added ammonium acetate (540 mg), and the mixture was stirred at 110° C. for 45 min. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated to give a crude product (218 mg). To a solution of the obtained crude product in tetrahydrofuran (5 mL) was added 1M hydrochloric acid (5 mL), and the mixture was stirred at 50° C. for 4 hr. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to preparative HPLC to give the title compound (155 mg, yield 78%) as a colorless amorphous solid. MS: 471 (MH+).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give a crude product (218 mg)
  7. stirringthe mixture was stirred at 50° C. for 4 hr
  8. washwashed with saturated aqueous sodium hydrogen carbonate
  9. washThe ethyl acetate layer was washed with saturated brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a4e00641d31e4f2a8ee5c3aafddbcbd9
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08318746B2

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