HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → N-(3-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | N-(3-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamide | HCID 118523949 | — |
| Solvent | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Product | N-(3-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamide | HCID 72944749 | 90.9% |
Reaction Steps
Using similar reaction conditions as described in step-iii of example-1, N-(3-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamide (250 mg, 0.39 mmol) was hydrolyzed with lithium hydroxide (66 mg, 1.57 mmol) in THF/water/methanol (5/4/3 ml) mixture to afford 170 mg (89.94% yield) of the pure product. 1H NMR (DMSO-d6, 300 MHz): δ 11.83 (s, 1H), 8.47-8.32 (m, 3H), 7.97 (s, 1H), 7.799-7.794 (d, 1H), 7.64-7.55 (m, 3H), 7.49-7.44 (m, 3H), 7.32-7.21 (m, 2H), 5.44 (s, 2H), 3.03 (s, 3H) MS: m/z=479.8 (M+1), HPLC: 73.14% in method A.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-c9d64063e168412f94bfecc430d4b763 |
| Source note | uspto-grants-2016_05 |