HuagongsheHuagongshe Chemistry Print Report · For research reference only
Thionyl Chloride → HCID 178422785, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-(Difluoromethyl)-2-fluoroaniline | HCID 67503527 | — |
| Reactant | HCID 178422815 | HCID 178422815 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178422785 | HCID 178422785 | 5.8% |
Reaction Steps
The title compound was prepared by following the same procedure as described for Example-108 using 2-[(2-chloro-6-fluorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-15, 0.150 g, 0.400 mmol), thionyl chloride (2.0 mL), 5-(difluoromethyl)-2-fluoroaniline (Intermediate-46, 0.097 g, 0.600 mmol), THF (5.0 mL) and DIPEA (2 mL). The obtained crude product was purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.012 g of the desired product. 1HNMR (DMSO-d6): δ 1.56 (s, 6H), 3.13 (s, 2H), 7.07 (t, J=55.5 Hz, 1H), 7.33-7.52 (m, 6H), 8.76 (d, J=6.9 Hz, 1H), 10.24 (s, 1H), 11.20 (s, 2H); MS [M+H]+: 519.20.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08519149B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-b25606bd9236485289d099d67513d7ba |
| Source note | uspto-grants-2013_08 |