Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 67173587 | HCID 67173587 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67085565 | HCID 67085565 | — |
Reaction Steps
To a solution of the product of step A in dichloromethane (0.9 mL) and methanol (0.1 mL) was added 2M HCl in diethyl ether (5 mL). The reaction mixture was stirred at ambient temperature overnight, filtered, washed with diethyl ether and dried in vacuo to give 2-(3,5-difluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (15 mg, 50%, AUC HPLC 98.0%) as an off-white solid: mp 230-235° C. dec; 1H NMR (CD3OD, 300 MHz) δ 8.32 (d, J=1.8 Hz, 1H), 7.77 (dd, J=8.7, 1.8 Hz, 1H), 7.57-7.61 (m, 3H), 7.20-7.28 (m, 1H), 5.32 (d, J=4.8 Hz, 1H), 4.55 (br s, 1H), 3.73 (s, 3H), 3.49 (dd, J=17.4, 4.5 Hz, 1H), 3.25-3.40 (m, 1H), 3.08 (d, J=17.4 Hz, 1H), 2.26-2.48 (m, 2H), 1.96-2.00 (m, 1H); ESI MS m/z 389 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08575186B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-0864a8c65a5d444a87dd8769ac38224d |
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| Source note | uspto-grants-2013_11 |
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