Hydrochloric Acid → HCID 178498897, Verbindung

HRID 1426971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426971
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]2[CH:20]=[CH:19][N:18]3[N:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[C:17]3[N:16]=2)[C:5]([O:8]C)=[N:6][CH:7]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:28].Cl>CO.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]2[CH:20]=[CH:19][N:18]3[N:21]=[CH:22][C:23]([C:24]([O:26][CH3:28])=[O:25])=[C:17]3[N:16]=2)[C:5]([OH:8])=[N:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 167693TrimethylsilyldiazomethaneHCID 66847769HCID 66847769, Verbindung

Produkt 1

HCID 178498897HCID 178498897, VerbindungAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a suspension of (R)-5-(2-(5-fluoro-2-methoxypyridin-3-yl) pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (Preparation B; 5.01 g, 14.0 mmol) in MeOH (150 mL) was added dropwise TMSCHN2 (8.41 mL, 16.8 mmol). The reaction was stirred for 30 minutes, and then quenched with 1 mL of acetic acid. The solvent was removed under reduced pressure and the residue was dried under high vacuum to give the crude methyl ester. To the crude methyl ester was added 4N HCl in dioxane (100 mL) and the reaction was sealed and heated to 90° C. for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in DCM (100 mL) and washed with saturated NaHCO3 (40 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude desired product (4.67 g, 93.2% yield). MS (apci) m/z=357.9 (M+H).

Aufarbeitung

  1. customquenched with 1 mL of acetic acid
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was dried under high vacuum
  4. customto give the crude methyl ester
  5. customthe reaction was sealed
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in DCM (100 mL)
  8. washwashed with saturated NaHCO3 (40 mL)
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e19ab080dcbd4bf8a9a8018ce7986d4e
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933084B2

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