HuagongsheHuagongshe Chemistry Print Report · For research reference only
Amantadine Hydrochloride → 1-[4-[N-(Adamant-1-yl)carbamoyl]-2-methoxybenzenesulfonyl]-3-cyclohexyl-5-ethoxy-1,3-dihydro-2H-benzimidazol-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Amantadine Hydrochloride | HCID 64150 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | 5-Ethoxy-1,3-dihydro-1-(2-methoxy-4-carboxybenzenesulfonyl)-3-cyclohexyl-2H-benzimidazol-2-one | HCID 15229042 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-[4-[N-(Adamant-1-yl)carbamoyl]-2-methoxybenzenesulfonyl]-3-cyclohexyl-5-ethoxy-1,3-dihydro-2H-benzimidazol-2-one | HCID 23364253 | 42.2% |
Reaction Steps
This compound is prepared by the procedure described in EXAMPLE 100 starting from 0.5 g of the compound obtained in EXAMPLE 13, 0.3 g of 1-aminoada- mantane hydrochloride, 0.5 g of BOP, 2 ml of DIPEA and 25 ml of DCM. It is chromatographed on silica using a DCM/MeOH mixture (99/1; v/v) as the eluent to give 0.27 g of the expected product after crystallization from an EtOH/iso ether mixture (80/20; v/v). M.p.=228° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05585394 |
| Source dataset | uspto-grants-1996_12 |
| ORD ID | ord-4175c1ac464942b48c2ca0fc26602194 |
| Source note | uspto-grants-1996_12 |