HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → N-(5-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | N-(5-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamide | HCID 90030463 | — |
| Solvent | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Product | N-(5-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamide | HCID 72944103 | 22.9% |
Reaction Steps
Using similar reaction conditions as described in step-iii of example-1, N-(5-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamide (120 mg, 0.180 mmol) was hydrolyzed by lithium hydroxide 38 mg, 0.904 mmol) in THF/methanol/water (15/7.5/4 ml) to yield 21 mg of the titled compound. 1H NMR (CDCl3, 400 MHz): δ 10.3 (s, 1H), 8.49-8.48 (d, 1H), 8.256-8.252 (d, 1H), 7.85 (s, 1H), 7.81-7.80 (d, 1H), 7.77 (s, 1H), 7.48-7.47 (d, 1H), 7.39-7.37 (dd, 1H), 7.26-6.91 (m, 5H), 5.42 (s, 2H), 3.96 (s, 3H), 3.01 (s, 3H). MS: m/z=510.1 (M+1), HPLC: 96.37% in method B.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-1ac6885e690548ca8b6e6af08b89460d |
| Source note | uspto-grants-2016_05 |