HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloride methanol → N-(5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)phenyl)methanesulfonamide hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloride methanol | HCID 21893726 | — |
| Reactant | tert-butyl 5-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-3-(methylsulfonamido)phenyl)-3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate | HCID 90030733 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | N-(5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl)phenyl)methanesulfonamide hydrochloride | HCID 72944426 | 68% |
Reaction Steps
Using similar reaction conditions as described in step-ii of example-7, tert-butyl 5-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-3-(methylsulfonamido)phenyl)-3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (21 mg, mmol) was deprotected in methanol/HCl in diethyl ether (2/1 ml) to afford 11 mg (68% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.859-8.853 (d, 1H), 8.736-8.73 (d, 1H), 8.37 (s, 1H), 8.33 (s, 1H), 8.00 (s, 1H), 7.867-7.861 (d, 1H), 7.66-7.63 (dd, 1H), 7.53-7.50 (d, 1H), 7.27-7.12 (m, 5H), 4.63-4.61 (t, 2H), 3.51-3.47 (t, 4H), 3.50-3.24 (m, 9H). MS: m/z=542.3 (M+1), HPLC: 98.49% in method B.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-feb6c034606248d6a23867d2db407392 |
| Source note | uspto-grants-2016_05 |