HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-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-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy phenyl)methanesulfonamide | HCID 90030711 | — |
| Solvent | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Product | N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamide | HCID 72944950 | 8.4% |
Reaction Steps
Using similar reaction conditions as described in step-iii of example-1, N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy phenyl)methanesulfonamide was hydrolyzed with lithium hydroxide (65 mg, 1.56 mmol) in THF/Methanol/water (10/3/2 mL). This yielded 22 mg (8.4% yield) of pure compound after purification by flash chromatography. 1H NMR (DMSO-d6, 300 MHz): δ 11.9 (s, 1H), 9.07 (s, 1H), 8.519-8.515 (d, 2H), 7.827-8.23 (d, 2H), 7.56-7.43 (m, 3H), 7.21-7.04 (m, 4H), 5.36 (s, 2H), 3.90 (s, 3H), 3.03 (s, 3H), 2.21-2.17 (d, 6H). MS: m/z=520.1 (M+1), HPLC: 95.74% (Method-B).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-36d52347433d426d8487146a6f4bdfc3 |
| Source note | uspto-grants-2016_05 |