HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-(Thiophen-2-yl)benzoic acid → (1R,6S)-8-(3,6-Dimethylpyrazin-2-yl)-3-{[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}-3,8-diazabicyclo[4.2.0]octane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-(Thiophen-2-yl)benzoic acid | HCID 5105623 | — |
| Reactant | 5-fluoro-2-(2H-1,2,3-triazol-2-yl)benzoic acid | HCID 67086948 | — |
| Reactant | (1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane | HCID 68156939 | — |
| Reactant | (1R,6S)-8-(3,6-Dimethyl-pyrazin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane | HCID 68157557 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (1R,6S)-8-(3,6-Dimethylpyrazin-2-yl)-3-{[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}-3,8-diazabicyclo[4.2.0]octane | HCID 52920050 | — |
Reaction Steps
The title compound was prepared in a manner analogous to Example 1, substituting (1R,6S)-8-(3,6-Dimethyl-pyrazin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane (Intermediate 10) for (1R,6S)8-(4,6-dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane and 5-fluoro-2-[1,2,3]triazol-2-yl-benzoic acid (Intermediate 13) for 2-thiophen-2-yl-benzoic acid. DCM was used in place of DMF. MS (ESI) mass calcd. For C21H22FN7O, 407.45; m/z found 408.2 [M+H]+. 1H NMR (CD3OD): 8.05-7.84 (m, 2H), 7.66-7.24 (m, 4H), 4.59-3.44 (m, 7H), 3.04-2.31 (m, 6H), 2.09-2.96 (m, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08680275B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-399d4c22bfa24cc8afed541d3e76b649 |
| Source note | uspto-grants-2014_03 |