HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 4-[(S)-2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-3-[6-(2,8-diaza-spiro[5.5]undec-2-yl)-4-methyl-1H-benzoimidazol-2-yl]-1H-pyridin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (S)-2-amino-1-(3-chlorophenyl)ethanol | HCID 9855591 | — |
| Reactant | 4-Chloro-3-[6-(2,8-diaza-spiro[5.5]undec-2-yl)-4-methyl-1H-benzoimidazol-2-yl]-1H-pyridin-2-one | HCID 136106993 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 4-[(S)-2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-3-[6-(2,8-diaza-spiro[5.5]undec-2-yl)-4-methyl-1H-benzoimidazol-2-yl]-1H-pyridin-2-one | HCID 136107027 | 47% |
Reaction Steps
A solution of 4-Chloro-3-[6-(2,8-diaza-spiro[5.5]undec-2-yl)-4-methyl-1H-benzoimidazol-2-yl]-1H-pyridin-2-one (16 mg, 0.039 mmol), (S)-2-amino-1-(3-chlorophenyl)-ethanol (20 mg, 0.117 mmol) and Et3N (16 mg, 0.156 mmol) in EtOH (0.5 mL) was heated at 80° C. for 16 h. After it was cooled to room temperature, the reaction mixture was filtered to furnish yellow solid that was washed with MeOH (3×3 mL). The yellow solid then was mixed with 3 mL MeOH and the mixture was heated at 100° C. for 1 h. After it was cooled to room temperature, the mixture was filtered to furnish yellow solid that was washed with MeOH (3×2 mL) to afford the title compound (10 mg, 47%). ESI-MS m/z 547 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08629147B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-53bc78b49d664e8f91dfbaca9acfe72e |
| Source note | uspto-grants-2014_01 |