HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Lithium Hydroxide → 3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Lithium Hydroxide | HCID 3939 | — |
| Edukt | 3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine | HCID 90031541 | — |
| Edukt | 3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine | HCID 90064901 | — |
| Edukt | 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride | HCID 118524085 | — |
| Lösungsmittel | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Produkt | 3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine | HCID 90030761 | 123,5% |
Reaktionsschritte
Using similar reaction conditions as described in step-iii of example-1, 3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (step 2 compound of example 133) (50 mg, 0.079 mmol) was hydrolyzed with lithium hydroxide (32 mg, 0.743 mmol) in THF/methanol/water (2/2/1 mL) to yield 46 mg (63.8% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.58 (s, 1H), 8.537-8.530 (d, 2H), 8.28 (s, 1H), 8.19-8.16 (dd, 1H), 8.00 (s, 1H), 7.77 (s, 1H), 7.22-7.19 (d, 1H), 6.88-6.85 (m, 3H), 5.43 (s, 2H), 3.94-3.90 (t, 4H), 3.41-3.37 (t, 4H). MS: m/z=472.3 (M+1), HPLC: 95.01% in method A.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09353107B2 |
| Quelldatensatz | uspto-grants-2016_05 |
| ORD ID | ord-89f2df9490134a7fb1094ffb9a7746af |
| Quellennotiz | uspto-grants-2016_05 |