HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Chlorobenzoic Acid → 5-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2-[2-chloro-5-(propionylamino)-phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Chlorobenzoic Acid | HCID 8374 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | 5-n-Butyl-2-[2-chloro-5-(propionylamino)-phenyl]-2,4-dihydro-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one | HCID 10348320 | — |
| Product | 5-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2-[2-chloro-5-(propionylamino)-phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one | HCID 10032820 | 65% |
Reaction Steps
Following the procedure of Example 51, 5-n-butyl-2-[2-chloro-5-(propionylamino)phenyl]-2,4-dihydro-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one (from Step E) was reacted with 2-chlorobenzoic acid (2 equivalents), CDI (2 equiv), and DBU (2 equiv). Purification of the crude product by flash chromatography on silica gel (gradient elution with 1-5% MeOH in CH2Cl2) gave a 65% yield of the title compound as a white solid, mp >152° C. (gradual); homogeneous by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 762 (M+K)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05411980 |
| Source dataset | uspto-grants-1995_05 |
| ORD ID | ord-9122465ffe244fae8a26b4332160440f |
| Source note | uspto-grants-1995_05 |