HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → N-(5-(3-(1-(3,5-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-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methane sulfonamide | HCID 90031267 | — |
| Solvent | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Product | N-(5-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamide | HCID 90031733 | 16.1% |
Reaction Steps
Using similar reaction conditions as described in step-iii of example-1, N-(5-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methane sulfonamide (105 mg, 0.1582 mmol) was hydrolyzed by lithium hydroxide (34 mg, 0.791 mmol) in THF/methanol/water (15/7.5/4 ml) to yield 13 mg of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.556-8.551 (d, 2H), 8.51-8.50 (d, 1H), 8.28 (s, 1H), 7.98 (s, 1H), 7.76-7.75 (m, 2H), 7.64-7.76 (dd, 1H), 7.22-7.20 (d, 1H), 6.94-6.84 (m, 2H), 5.44 (s, 2H), 3.99 (s, 3H), 2.99 (s, 3H). MS: m/z=510.1 (M+1), HPLC: 98.06% in method B.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-b47af581883b4a4e8591aa0d7e1996c6 |
| Source note | uspto-grants-2016_05 |