HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium borohydride → HCID 178478143, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 5-Chloropyridine-2-carboxaldehyde | HCID 10103267 | — |
| Reactant | 3-Amino-5-(3,5-dichloroanilino)-s-triazole | HCID 72714614 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 178478143 | HCID 178478143 | 90% |
Reaction Conditions
| Temperature | -20 °C |
|---|
Reaction Steps
A solution of N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 2 (70 mg, 287 μmol) and 5-chloro-2-formylpyridine (60 mg, 424 μmol) in MeOH (3 ml) was stirred at room temperature for one day and then at 45° C. for two days to give a suspension, cooled to −20° C. and was filtered to collect the solid. The solid was re-suspended in MeOH (5 ml), NaBH4 (163 mg, 4.3 mmol) was added in a few portions and the reaction was stirred for 1 hour. The solvent was removed, and the reaction mixture was redissolved in EtOAc (5 ml) and washed with water (2×4 ml), dried over MgSO4 and concentrated. Crystallization from DCM afforded a white solid as desired product (96.6 mg, 90% yield). MS +m/z: 369 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09428469B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-d2f3481082064c819b77f23375b73b89 |
| Source note | uspto-grants-2016_08 |