HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-(5-Trifluoromethyl-1H-indol-3-YL)acetic acid → (S)-N-(1-(4-(4-chlorophenyl)isoxazol-3-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-hydroxy-1H-indol-3-yl)acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-(5-Trifluoromethyl-1H-indol-3-YL)acetic acid | HCID 22490726 | — |
| Reactant | 1-(2-(4-Chlorophenyl)oxazol-5-yl)-2-(3,5-difluorophenyl)ethanamine hydrochloride | HCID 90280320 | — |
| Reactant | (S)-1-(4-(4-chlorophenyl)isoxazol-3-yl)-2-(3,5-difluorophenyl)ethanamine | HCID 90280390 | — |
| Reactant | N-(1-(2-(4-chlorophenyl)oxazol-5-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-fluoro-1H-indol-3-yl)acetamide | HCID 90290342 | — |
| Product | (S)-N-(1-(4-(4-chlorophenyl)isoxazol-3-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-hydroxy-1H-indol-3-yl)acetamide | HCID 90281437 | — |
Reaction Steps
The title compound was prepared according to the method presented in the synthesis of 19F substituting 2-(5-hydroxy-1H-indol-3-yl)acetic acid for 2-(5-(trifluoromethyl)-1H-indol-3-yl)acetic acid and (S)-1-(4-(4-chlorophenyl)isoxazol-3-yl)-2-(3,5-difluorophenyl)ethanamine for 19E to provide the desired compound (26): 1H NMR (400 MHz, DMSO) δ 10.46 (s, 1H), 9.04 (s, 1H), 8.65 (d, 1H), 7.35-7.20 (m, 3H), 7.06 (d, 1H), 6.92 (t, 1H), 6.87 (d, 1H), 6.77 (d, 1H), 6.71 (d, 2H), 6.54 (dd, 1H), 5.25 (q, 1H), 3.39-3.25 (m, 2H), 3.08 (d, 2H); MS (m/z) 508.8 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09220710B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-6e29e25fc4e54a0498ba78a114891667 |
| Source note | uspto-grants-2015_12 |