HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → N-(3-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-dimethoxyphenyl)methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | N-(3-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-dimethoxy phenyl)methanesulfonamide | HCID 90030283 | — |
| Solvent | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Product | N-(3-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-dimethoxyphenyl)methanesulfonamide | HCID 72943388 | 25.9% |
Reaction Steps
Using similar reaction conditions as described in step-iii of example-1, N-(3-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-dimethoxy phenyl)methanesulfonamide (40 mg, 0.05 mmol) was hydrolyzed by lithium hydroxide (23.8 mg, 0.5 mmol), THF/Methanol/water (12/4/4 ml) to afford 7 mg (25.9% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.5 (b, 1H), 8.181-8.177 (d, 1H), 7.525 (s, 1H), 7.356-7.334 (m, 2H), 6.991-6.957 (m, 3H), 6.9-6.85 (m, 1H), 5.363 (s, 2H), 3.930 (s, 3H), 3.499 (s, 3H), 3.184 (s, 1H), 2.231-2.204 (d, 6H). MS: m/z=550.0 (M+1); HPLC: 94.463% in method A.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-f10d631126ef46ccb4fed133429f9809 |
| Source note | uspto-grants-2016_05 |