HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → N-(3-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methane sulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | N-(3-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methane sulfonamide | HCID 90030771 | — |
| Solvent | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Product | N-(3-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methane sulfonamide | HCID 72944750 | 8.8% |
Reaction Steps
Using similar reaction conditions as described in step-iii of example-1, N-(3-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methane sulfonamide (300 mg, 0.473 mmol) was hydrolyzed with lithium hydroxide (40 mg, 0.946 mmol) in THF/water/methanol (15/10/5 ml) mixture to afford 20 mg (8.8% yield) of the desired compound. 1H NMR (DMSO-d6, 400 MHz): δ 11.82 (s, 1H), 9.82 (s, 1H), 8.48-8.47 (d, 1H), 8.43 (s, 1H), 8.355-8.350 (d, 1H), 8.00 (s, 1H), 7.71-7.80 (d, 1H), 7.53-7.46 (m, 3H), 7.25-7.23 (m, 2H), 6.98-6.97 (d, 2H), 5.42 (s, 2H), 3.05 (s, 3H). MS: m/z=479.8 (M+1), HPLC: 94.78% (Method-B).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-cd23dee7cc8a4d489f02c73282a47af3 |
| Source note | uspto-grants-2016_05 |