Sodium methanolate methanol → (S)-tetrahydrofuran-3-yl 3-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)azetidine-1-carboxylate

HRID 526891

Reaktionsgleichung

Reaktionsgleichung von HRID 526891
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][CH:18]4[CH2:21][N:20]([C:22]([O:24][C@H:25]5[CH2:29][CH2:28][O:27][CH2:26]5)=[O:23])[CH2:19]4)[C:14]([F:30])=[CH:13][N:12]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.C[O-].[Na+].CO>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][CH:18]4[CH2:19][N:20]([C:22]([O:24][C@H:25]5[CH2:29][CH2:28][O:27][CH2:26]5)=[O:23])[CH2:21]4)[C:14]([F:30])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 23694274Sodium methanolate methanolHCID 67287100(S)-tetrahydrofuran-3-yl 3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)azetidine-1-carboxylate

Produkt 1

HCID 68007196(S)-tetrahydrofuran-3-yl 3-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)azetidine-1-carboxylateAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(S)-tetrahydrofuran-3-yl 3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)azetidine-1-carboxylate, 6d, was dissolved in methanol (2 mL) and then treated with of 25% sodium methoxide/methanol (0.5 mL) and heated at 60° C. in sealed tube. LCMS showed complete reaction after 10 minutes. The resulting solution was quenched with aqueous saturated NH4Cl solution (0.5 mL) then evaporated to dryness and the residue dissolved in DMSO and purified by reverse phase HPLC (ammonium formate buffer) to afford 25.9 mg (55% yield) of the desired product, 422, as a solid.

Aufarbeitung

  1. customreaction after 10 minutes
  2. customThe resulting solution was quenched with aqueous saturated NH4Cl solution (0.5 mL)
  3. customthen evaporated to dryness
  4. dissolutionthe residue dissolved in DMSO
  5. custompurified by reverse phase HPLC (ammonium formate buffer)

Quellen und Nachweise

ORD-Eintrag
ord-3dc9bcaf090543bc9c50cf17c5763dac
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345708B2

Verknüpfte Notizen

Wird geladen…