HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyrrolidine → 1-(Cyclohexyl)methyl-7-methoxy-3-{5-[(pyrrolidin-1-yl)methyl]-[1,3,4]-thiadiazol-2-yl}-1H-indole, hydrochloride salt
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | 3-(5-chloromethyl-[1,3,4]thiadiazol-2-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole | HCID 68702053 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-(Cyclohexyl)methyl-7-methoxy-3-{5-[(pyrrolidin-1-yl)methyl]-[1,3,4]-thiadiazol-2-yl}-1H-indole, hydrochloride salt | HCID 131728077 | 40% |
Reaction Steps
To a solution of 3-(5-chloromethyl-[1,3,4]thiadiazol-2-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole (93 mg, 0.25 mmol) in tetrahydrofuran was added pyrrolidine (0.101 ml, 1.235 mmol) and the mixture subjected to microwave irradiation at 150° C. for 5 minutes. The resulting reaction mixture was purified by flash column chromatography to give the title compound (42 mg, 0.1 mmol) as the free base. The free base was dissolved in dichloromethane and hydrogen chloride (1M solution in diethyl ether; 1 ml, 1 mmol) was added. The excess reagent and solvent were removed in vacuo to afford the title compound as a 1:1 hydrochloride salt.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07700634B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-88350d5249dc4614aeb2630dfa731e93 |
| Source note | uspto-grants-2010_04 |