HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 4-[4-(2-{[(3R,3aR,6R,6aR)-6-Hydroxy-hexahydrofuro[3,2-b]furan-3-yl]oxy}-6-chloro-3H-imidazo[4,5-b]pyridin-5-yl)phenyl]-N,N-dimethyl-benzenesulfonimidamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | N-({4-[4-(2-{[(3R,3aR,6R,6aR)-6-Hydroxy-hexahydrofuro[3,2-b]furan-3-yl]oxy}-6-chloro-3-{[2-(trimethylsilyl)ethoxy]methyl}imidazo[4,5-b]pyridin-5-yl)phenyl]phenyl}(dimethylamino)oxo-lambda6-sulfanylidene)-2,2,2-trifluoroacetamide | HCID 131736745 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-[4-(2-{[(3R,3aR,6R,6aR)-6-Hydroxy-hexahydrofuro[3,2-b]furan-3-yl]oxy}-6-chloro-3H-imidazo[4,5-b]pyridin-5-yl)phenyl]-N,N-dimethyl-benzenesulfonimidamide | HCID 178486127 | — |
Reaction Steps
A mixture of N-({4-[4-(2-{[(3R,3aR,6R,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl]oxy}-6-chloro-3-{[2-(trimethylsilyl)ethoxy]methyl}imidazo[4,5-b]pyridin-5-yl)phenyl]-phenyl}(dimethylamino)oxo-λ6-sulfanylidene)-2,2,2-trifluoroacetamide (22 mg) and trifluoroacetic acid (0.30 mL) in dichloromethane (1.00 mL) is stirred over night at room temperature. The reaction mixture is concentrated in vacuo and the residue is dissolved in methanol. Aqueous Na2CO3 solution (2 N; 60 μL) is added and the mixture is stirred for 1 h. The reaction mixture is filtered and the crude product is purified by preparative HPLC to give the title compound. LC (method 1): tR=0.86 min; Mass spectrum (ESI+): m/z=556 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09422312B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-22fc5e80a5f94d979ea376e2d4cab7d4 |
| Source note | uspto-grants-2016_08 |