HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → 2-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)acetonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | 2-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl) acetonitrile | HCID 90031508 | — |
| Reactant | 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride | HCID 118524085 | — |
| Solvent | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Product | 2-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)acetonitrile | HCID 72944753 | 33.3% |
Reaction Steps
Using similar reaction conditions as described in step-iii of example-1, 2-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl) acetonitrile (60 mg, 0.092 mmol) was hydrolyzed by lithium hydroxide (8 mg, 0.185 mmol) in THF/methanol/water (5/1/1 ml) to yield 15 mg (33.3% yield) of the titled compound. 1H NMR (CDCl3, 400 MHz): δ 9.19 (s, 1H), 8.50-8.47 (dd, 2H), 8.128-8.123 (d, 1H), 7.86 (s, 1H), 7.79-7.76 (dd, 1H), 7.70 (s, 1H), 7.447-7.441 (d, 1H), 7.35-7.30 (m, 1H), 7.10-6.90 (m, 3H), 6.80-6.78 (d, 1H), 5.39 (s, 2H), 3.70-3.67 (t, 4H), 3.61 (s, 2H), 2.76-2.74 (t, 4H). MS: m/z=493.4 (M+1), HPLC: 97.07% in method A.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-a35c80e5746943308b4b4b58b2f600a7 |
| Source note | uspto-grants-2016_05 |