HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → N-(1-(azetidin-3-yl)-3-(5-fluoro-1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)benzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | tert-butyl 3-(3-(5-fluoro-1-methylindolin-6-yl)-4-(phenylsulfonamido)-1H-pyrrolo[2,3-b]pyridin-1-yl)azetidine-1-carboxylate | HCID 86720287 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-(1-(azetidin-3-yl)-3-(5-fluoro-1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)benzenesulfonamide | HCID 71090140 | 97.4% |
Reaction Steps
To a solution of tert-butyl 3-(3-(5-fluoro-1-methylindolin-6-yl)-4-(phenylsulfonamido)-1H-pyrrolo[2,3-b]pyridin-1-yl)azetidine-1-carboxylate (D33) (489 mg, 0.847 mmol) in DCM (8 mL) was added 4M HCl in dioxane (4.23 mL, 16.93 mmol). The final mixture was stirred at RT for 6 hours. The mixture was concentrated in vacuo. The residue was dissolved in MeOH and passed through a SCX cartridge eluting with MeOH followed by 2M ammonia in MeOH to give the title compound (394 mg). LCMS (A): m/z (M+H)+ 478, C25H24FN5O2S requires 477 (acidic).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08877742B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-fa3208f4243a4f329eb74e3a932cccbb |
| Source note | uspto-grants-2014_11 |