HuagongsheHuagongshe Chemistry Print Report · For research reference only
Oxalyl chloride → HCID 54562838, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]- | HCID 18348849 | — |
| Reactant | HCID 18348940 | HCID 18348940 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 54562838 | HCID 54562838 | 64.8% |
Reaction Steps
2M Oxalyl chloride solution in dichloromethane (0.110 ml) and dry DMF (0.002 ml) were added to a stirred suspension of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.060 g) in dry dichloromethane (1 ml) under nitrogen. After 5 min DIPEA (0.090 ml) was added followed after a further 40 min by 2-fluorophenyl-(3-tetrazol-2-yl-propyl)-amine (0.066 g) and DMAP (0.002 g). After 40 h the solvent was evaporated and the residue was purified by flash chromatography, eluting with dichloromethane:methanol (98:2 v/v) to give the title compound as a viscous yellow oil (0.059 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06326386B1 |
| Source dataset | uspto-grants-2001_12 |
| ORD ID | ord-85826d384cdb49bb950bf26597bad7d9 |
| Source note | uspto-grants-2001_12 |