HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-Methoxy-3-[3-(2-methoxy-pyridin-4-yl)-1-trityl-1H-indazol-5-ylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 3-(2-methoxypyridin-4-yl)-1-trityl-1H-indazol-5-ylamine | HCID 58372000 | — |
| Reactant | 1-[(Tert-butoxy)carbonyl]-3-methoxypyrrolidine-3-carboxylic acid | HCID 67345827 | — |
| Solvent | dichloromethane N,N-dimethylformamide | HCID 22350042 | — |
| Product | 3-Methoxy-3-[3-(2-methoxy-pyridin-4-yl)-1-trityl-1H-indazol-5-ylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 67343473 | — |
Reaction Steps
To the stirred suspension of 3-methoxy-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 6BV (4.16 mmole, crude) in DMF/DCM (25 mL/25 mL), 3-(2-methoxypyridin-4-yl)-1-trityl-1H-indazol-5-ylamine 5BV (2.008 g, 4.16 mmole) and Et3N (2.9 mL, 21 mmole) were added at r.t. under dry N2 gas followed by HATU (3.16 g, 8.32 mmole). The mixture was stirred at r.t. under dry N2 gas overnight. The mixture was partitioned between 1:1 EtOAc and sat. NaHCO3 solution. The organic phase was separated, washed with brine, dried over MgSO4 and evaporated to dryness. The crude solid was purified on RediSep 120 g cartridge eluting with 10-25% EtOAc/Hexanes to yield a brown solid 7BV (2.95 g, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08716483B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-03ad55f06a0d4c35844b525971cc1e00 |
| Source note | uspto-grants-2014_05 |