HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylamine → 1-[3-tert-Butyl-1'-(2-dimethylamino-ethyl)-3'-triisopropylsilanyloxymethyl-1'H-[1,4']bipyrazolyl-5-yl]-3-{(1S,4R)-4-[3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | HCID 123809205 | HCID 123809205 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-[3-tert-Butyl-1'-(2-dimethylamino-ethyl)-3'-triisopropylsilanyloxymethyl-1'H-[1,4']bipyrazolyl-5-yl]-3-{(1S,4R)-4-[3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea | HCID 123177122 | 82.9% |
Reaction Steps
A solution of Intermediate 74j (104 mg, 0.11 mmol) in THF (0.5 mL) was treated with dimethylamine (2M in THF, 0.57 mL, 1.1 mmol) and the mixture was stirred at RT over the weekend. The mixture was evaporated in vacuo and the residue was partitioned between DCM and water. The aqueous layer was then extracted with DCM (2×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-7% [2M NH3 in MeOH] in DCM, to give the title compound (79 mg, 81%). LCMS (Method 3): Rt 3.46 min, m/z 866.6 [MH+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09440974B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-22b43f98ae5f47858a5be3db7dd97165 |
| Source note | uspto-grants-2016_09 |