Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 1-Piperazinecarboxylic acid, ethyl ester | HCID 8431 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 11563567 | HCID 11563567 | — |
| Solvent | 1,1-Dichloroethane | HCID 6365 | — |
| Product | HCID 11628613 | HCID 11628613 | 38% |
Reaction Steps
To a solution of 7-formyl-1-methyl-1H-indole-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide (see Example 2, 30 mg, 0.066 mmol) and ethyl N-piperazinocarboxylate (104 mg, 0.66 mmol) in dichloroethane (2 mL) was added acetic acid (0.1 mL). The mixture was stirred at room temperature for 4 h. Sodium triacetoxyborohydride (35 mg, 0.156 mmol) was then added to the reaction mixture. The reaction was stirred overnight at room temperature and then quenched with saturated NaHCO3 solution. The mixture was then extracted with EtOAc and dichloromethane in sequence, dried over Na2SO4 and concentrated. The residue was purified by preparative-TLC, eluting with EtOAc-hexane, 1:1, providing 15 mg (38%) of the title compound. ESI MS m/z 600.37 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07470692B2 |
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| Source dataset | uspto-grants-2008_12 |
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| ORD ID | ord-3ae6967227ca4e06b14dee01792f7869 |
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| Source note | uspto-grants-2008_12 |
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