HuagongsheHuagongshe Chemistry Print Report · For research reference only
Thionyl Chloride → HCID 178422738, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-Cyclopropyl-2-fluoroaniline | HCID 67503677 | — |
| Reactant | HCID 178422815 | HCID 178422815 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178422738 | HCID 178422738 | 22.1% |
Reaction Steps
The title compound was prepared by following the 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-cyclopropyl-2-fluoroaniline (Intermediate-47, 0.090 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 0.045 g of the desired product. 1HNMR (DMSO-d6): δ 0.62-0.63 (m, 2H), 0.93-0.96 (m, 2H), 1.54 (s, 6H), 1.93 (m, 1H), 3.13 (s, 2H), 6.80 (s, 1H), 7.14-7.50 (m, 5H), 8.24 (t, J=7.8 Hz, 1H), 10.07 (s, 1H), 11.20 (s, 2H); MS [M+H]+: 509.23.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08519149B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-b0fbf248074e4072957191ba88f75130 |
| Source note | uspto-grants-2013_08 |