HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxyphenyl)-3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate → N-(2-methoxy-5-(3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxyphenyl)-3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate | HCID 131735669 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Diethyl ether methanol | HCID 21864698 | — |
| Product | N-(2-methoxy-5-(3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide | HCID 72944104 | 29% |
Reaction Steps
Using similar reaction conditions as described in step-ii of example-7, tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxyphenyl)-3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (60 mg, 0.219 mmol) was deprotected in HCl in ether/MeOH (1/3 ml) to afford 13 mg (29% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.78 (s, 2H), 8.53 (s, 2H), 8.42-8.37 (m, 2H), 8.02 (s, 1H), 8.00-7.94 (m, 1H), 7.77-7.76 (m, 2H), 7.62-7.59 (dd, 1H), 7.24-7.21 (d, 1H), 5.66 (s, 2H), 3.98 (s, 3H), 2.99 (s, 3H). MS: m/z=475.1 (M+1), HPLC: 97.36% in method A.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-6f63cde017654931b5a99137141d65ee |
| Source note | uspto-grants-2016_05 |