Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 5-Methylfurfural | HCID 12097 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 3-Amino-5-(3,5-dichloroanilino)-s-triazole | HCID 72714614 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 178425520 | HCID 178425520 | 74% |
Reaction Steps
A solution of N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 2 (60 mg, 246 μmol) and 5-methylfuran-2-carbaldehyde (111.2 mg, 1.0 μmol) in MeOH (3 ml) was stirred 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 (55.8 mg, 1.47 mmol) was added 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 in vacuo. Trituration with DCM afforded an off white solid as desired product (61.3 mg, 74% yield). MS +m/z: 338 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09428469B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-eb8b33391c4e4a04871f5e3fbad206ef |
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| Source note | uspto-grants-2016_08 |
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