Reaktion #675377

Reaktionsgleichung

6-Chloro-3-(methylsulfonyl)-1H-pyrazolo[4,3-c]pyridine

(R)-1-(1-phenylethyl)urea

Potassium t-butoxide

→

(R)-1-(3-(methylsulfonyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe vial was evacuated
2. 2
   workup.ADDITIONback-filled with N2 (×3)
3. 3
   SonstigeThe crude reaction mixture
4. 4
   Filtrationwas filtered through a Si-Thiol cartridge (6 mL, 500 mg)
5. 5
   Sonstigeto remove excess Pd
6. 6
   EinengenThe filtrate was concentrated in vacuo
7. 7
   workup.DISSOLUTIONdissolved in DMSO/MeOH (with a few drops of TFA)
8. 8
   Sonstigepurified by mass
9. 9
   workup.ADDITIONThe fractions containing pure product
10. 10
    Einengenwere concentrated in vacuo

Vorschrift

6-Chloro-3-(methylsulfonyl)-1H-pyrazolo[4,3-c]pyridine (45 mg, 0.194 mmol), (R)-1-(1-phenylethyl)urea (38.3 mg, 0.233 mmol), and BrettPhos pre-catalyst (21.72 mg, 0.027 mmol) were taken up in THF (650 μL) in a 1.5 mL microwave vial. Potassium t-butoxide (1 M in THF, 583 μL, 0.583 mmol) was added and the vial was evacuated and back-filled with N2 (×3). The reaction mixture was stirred at 60° C. for 18 h. The crude reaction mixture was filtered through a Si-Thiol cartridge (6 mL, 500 mg) to remove excess Pd. The filtrate was concentrated in vacuo, dissolved in DMSO/MeOH (with a few drops of TFA), and purified by mass triggered, reverse phase prep-HPLC. The fractions containing pure product were concentrated in vacuo to afford (R)-1-(3-(methylsulfonyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. For C16H17N5O3S [M+1]+ 360. found 360. 1H NMR (500 MHz, DMSO-d6) δ 9.21 (s, 1H), 8.92 (s, 1H), 7.87 (s, 1H), 7.50 (br s, 5H), 4.92-4.80 (m, 1H), 3.38 (s, 3H) 1.40 (d, J=7.0 Hz, 3H).

Quelle