Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-(2-Chlorobenzoyl)-3,3-bis(methylsulfanyl)prop-2-enenitrile | HCID 2819091 | — |
| Reactant | (S)-1-[(3-amino-hexahydro-2-oxo-1H-azepin-1-yl)acetyl]pyrrolidine | HCID 12047820 | — |
| Reactant | 2-Methyl-1-benzofuran-5-amine--hydrogen chloride (1/1) | HCID 21696866 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 70032059 | HCID 70032059 | 39% |
Reaction Steps
Triethylamine (0.04 mL, 0.29 mmol) was added to a suspension of 2-methyl-5-benzofuranamine·HCl (40 mg, 0.22 mmol) and acetonitrile (0.5 mL) at room temperature, which resulted in a clear solution. To the solution was added α-[bis(methylthio)methylene]-2-chloro-β-oxobenzenepropanenitrile(56 mg, 0.20 mmol) and the resulting solution was heated at 50° C. for 1 hour. To this mixture was added 1-[[(3S)-3-aminohexahydro-2-oxo-1H-azepin-1-yl]acetyl]pyrrolidine (47 mg, 0.20 mmol) and the resulting mixture was heated at 70° C. After 4 h, the mixture was concentrated in vacuo. The residue was purified by flash chromatography (silica, 0 to 2% methanol/dichloromethane) to give the title compound as a white solid (44 mg, 39%): MS (ESI, pos. ion spectrum) m/z 574/576 (M+H); HPLC (method A) tR 4.03 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06544981B2 |
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| Source dataset | uspto-grants-2003_04 |
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| ORD ID | ord-fbb2e25324634e06bebe94cd3ba3d055 |
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| Source note | uspto-grants-2003_04 |
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