HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → 5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxypyridin-3-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | 5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy pyridin-3-amine | HCID 118524036 | — |
| Solvent | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Product | 5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxypyridin-3-amine | HCID 90030634 | 17.1% |
Reaction Steps
Using similar reaction conditions as described in step-iii of example-1, 5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxypyridin-3-amine (80 mg, 0.14 mmol) was hydrolyzed with lithium hydroxide (12 mg, 0.28 mmol) in THF/methanol/water (2/2/1 mL) to yield 10 mg (17.1% yield) after purification by preparative TLC(Silicagel-1000 micron) using 5% methanol in chloroform as eluent. 1H NMR (CD3OD, 300 MHz): δ 8.37 (s, 1H), 8.27 (s, 1H), 8.17 (s, 1H), 7.91 (s, 1H), 7.717-7.712 (d, 1H), 7.61 (s, 1H), 7.36-7.29 (m, 2H), 7.10-6.98 (m, 3H), 5.41 (s, 2H), 4.00 (s, 3H). MS: m/z=415.2 (M+1), HPLC: 88.73% in method B.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-a006b84c09a94b058d260ed0853cb320 |
| Source note | uspto-grants-2016_05 |