HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanesulfonyl chloride → Methanesulfonic acid 1-(6-{(1R,4S)-4-[3-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-ureido]-1,2,3,4-tetrahydro-naphthalen-1-yloxy}-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-piperidin-4-ylmethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-{(1S,4R)-4-[3-(4-hydroxymethyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea | HCID 117729043 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methanesulfonic acid 1-(6-{(1R,4S)-4-[3-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-ureido]-1,2,3,4-tetrahydro-naphthalen-1-yloxy}-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-piperidin-4-ylmethyl ester | HCID 117728708 | 109.5% |
Reaction Steps
Methanesulfonyl chloride (8.8 μL, 0.13 mmol) was added to a solution of Intermediate 14g (50 mg, 0.08 mmol) and DIPEA (46 μL, 0.26 mmol) in DCM (1.5 mL) and the reaction mixture was stirred at RT for 1 h. The mixture was diluted with DCM (5 mL) and washed with water (3×5 mL). The organic layer was passed through a phase separator and concentrated in vacuo to afford the title compound (57 mg, 100%). LCMS (Method 3): Rt: 3.21 min, m/z 651 [MH+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359354B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-b5c7a33b2b04429cad29ed424935e6e2 |
| Source note | uspto-grants-2016_06 |