HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethoxyethylamine → 1-Ethyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzo-imidazole-5-carboxylic acid (2-ethoxy-ethyl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethoxyethylamine | HCID 66970 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Reactant | 1-ethyl-2-(6-trifluoromethoxybenzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid | HCID 58397667 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-Ethyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzo-imidazole-5-carboxylic acid (2-ethoxy-ethyl)-amide | HCID 77106444 | 51.4% |
Reaction Steps
1-Ethyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzo-imidazole-5-carboxylic acid (2-ethoxy-ethyl)-amide (60.0 mg) was prepared by following General Procedure F starting from 1-ethyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid (100.0 mg), 2-ethoxy-ethylamine (30.0 mg), DPPA (85.0 mg), and DIEA (0.1 mL) in DMF (1.0 mL). LCMS: m/z 495; and 1H NMR (CD3OD, 400 MHz): δ 7.96 (1H, d), 7.77-7.75 (2H, m), 7.65 (1H, d), 7.43-7.41 (1H, m), 7.26-7.24 (1H, m), 4.27-4.26 (2H, q), 3.66-3.64 (2H, m), 3.59-3.55 (4H, m), 1.43-1.39 (3H, t), 1.23-1.20 (3H, t), 2 —NH proton signals were not observed.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08759535B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-7e0151a3c9f84895bb30a1076d793b63 |
| Source note | uspto-grants-2014_06 |