HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → N-(2-methoxy-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-methoxy-5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide | HCID 118523955 | — |
| Solvent | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Product | N-(2-methoxy-5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamide | HCID 72943991 | 17.2% |
Reaction Steps
Using similar reaction conditions as described in step-iii of example-1, N-(2-methoxy-5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide (100 mg, 0.155 mmol) was hydrolyzed by lithium hydroxide (13 mg, 0.311 mmol) in THF/methanol/water (5/1/2 mL) to afford 13 mg of the titled compound. 1H NMR (DMSO-d6, 400 MHz): δ 9.07 (s, 1H), 8.45-8.44 (d, 1H), 8.186-8.182 (d, 1H), 8.13, s 1H), 7.89 (s, 1H), 7.716-7.710 (d, 1H), 7.60-7.59 (m, 2H), 7.31-7.28 (m, 2H), 7.24-7.19 (m, 4H), 4.43-4.39 (t, 2H), 3.91 (s, 3H), 3.20-3.16 (t, 2H), 3.02 (s, 3H). MS: m/z=487.8 (M+1), HPLC: 95.48% in method A.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-127f99daf0b043e797c20db812db048b |
| Source note | uspto-grants-2016_05 |