HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → (2(S)-Pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-(4-thiophen-2-yl-phenyl)-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-(Thiophen-2-yl)benzoic acid | HCID 736498 | — |
| Reactant | (S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine | HCID 853152 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Solvent | dichloromethane N,N-dimethylformamide | HCID 22350042 | — |
| Product | (2(S)-Pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-(4-thiophen-2-yl-phenyl)-methanone | HCID 11493848 | 35% |
Reaction Steps
The title compound is prepared in a manner substantially analogous to General Procedure D in 10 mL 10% DMF/dichloromethane using 4-(thiophen-2-yl)-benzoic acid (CAS 29886-62-2) (182 mg, 0.89 mmol), EDC-HCl (254 mg, 1.33 mmol), HOBt (180 mg, 1.33 mmol), DIEA (0.39 mL, 2.22 mmol) and (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (116 mg, 10.0 mmol) to give the title compound (90 mg, 35% yield). MS (ES+) 341.2 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07705025B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-412dbde9c74e4402a52a25f6dc0f6adc |
| Source note | uspto-grants-2010_04 |