HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloride methanol → N-(5-(2-cyclopropyl-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 | Hydrochloride methanol | HCID 21893726 | — |
| Reactant | tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxyphenyl)-2-cyclopropyl-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate | HCID 131735666 | — |
| Product | N-(5-(2-cyclopropyl-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamide | HCID 72943389 | 8.18% |
Reaction Steps
tert-butyl5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxyphenyl)-2-cyclopropyl-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (150 mg) was hydrolyzed with methanol/HCl (5 ml) at 0° C. and purified by prep HPLC to afford 9 mg (8.18% yield) of the pure required product. 1H NMR (CD3OD, 400 MHz): δ 8.32-8.31 (s, 1H), 7.65-7.64 (d, 1H), 7.54-7.7.53 (d, 1H), 7.42-7.37 (q, 1H), 7.06-6.94 (m, 3H), 6.88-6.86 (d, 1H), 5.39 (s, 2H), 3.85 (s, 3H), 3.82 (s, 3H), 2.14 (s, 3H), 2.04 (s, 3H), 1.94-1.93 (m, 1H), 1.04-0.90 (m, 4H). MS: m/z=560.0 (M+1), HPLC Purity: 78.69% Method: B.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-bd676de5eaa24bb7a84638cf65f1e9b2 |
| Source note | uspto-grants-2016_05 |