HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → N-(2-fluoro-5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | N-(2-fluoro-5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide | HCID 118523937 | — |
| Solvent | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Product | N-(2-fluoro-5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamide | HCID 72944218 | 37.6% |
Reaction Steps
Using similar reaction conditions as described in step-iii of example-1, N-(2-fluoro-5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide (145 mg, 0.230 mmol) was hydrolyzed by lithium hydroxide (48 mg, 1.15 mmol) in THF/methanol/water (15/5/5 ml) to yield 41 mg (37.6% yield) of the titled compound after purification by preparative TLC(Silicagel-1000 micron) using 50% ethyl acetate in hexane as eluent. 1H NMR (CD3OD, 300 MHz): δ 8.44-8.40 (d, 1H), 8.108-8.101 (d, 1H), 7.83-7.74 (m, 2H), 7.58-7.50 (m, 2H), 7.40-7.10 (m, 5H), 4.46-4.42 (t, 2H), 3.20-3.16 (t, 2H), 3.06 (s, 3H). MS: m/z=476.5 (M+1), HPLC: 93.52% in method A.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-c8a3980e1a5e4f6fb66a1e051cf74a8d |
| Source note | uspto-grants-2016_05 |