Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | Aminomalononitrile p-toluenesulphonate | HCID 563049 | — |
| Reactant | 3-amino-N-cyclopropyl-4-methylbenzamide | HCID 11983854 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl orthoformate | HCID 31214 | — |
| Product | HCID 58088961 | HCID 58088961 | 30.2% |
Reaction Steps
A mixture of 3-amino-N-cyclopropyl-4-methyl-benzamide (380 mg, 2.0 mmol) in 2.0 mL of triethyl orthoformate was stirred at 120° C. in microwave for 20 minutes. The solvent was removed under reduced pressure. The residue was dissolved in 5 mL of acetic acid and then was added aminomalononitrile p-toluenesulfonate (506 mg, 2.0 mmol) and sodium acetate (164 mg, 2.0 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with 20 mL of water and the resulting precipitate was filtered to give 3-(5-amino-4-cyano-imidazol-1-yl)-N-cyclopropyl-4-methyl-benzamide 3A as a colorless solid (170 mg, 30%). HPLC tR=1.39 min; MS m/z 282 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07569571B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-ef704ae30cf442228a3f150a7a020beb |
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| Source note | uspto-grants-2009_08 |
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