Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 5-Aminoquinoline | HCID 11911 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 178520976 | HCID 178520976 | — |
| Reactant | HCID 178520978 | HCID 178520978 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | HCID 178523758 | HCID 178523758 | — |
Reaction Steps
To a solution of trans-N-(4-formyl-cyclohexyl)-3-trifluoromethyl-benzamide (prepared analogously to trans-2-chloro-N-(4-formyl-cyclohexyl)-5-trifluoromethyl-benzamide (Ex. 1 step 3) from the appropriate starting compounds) (100 mg, 0.33 mmol) and 5-aminoquinoline (48 mg, 0.33 mmol) in dry 1,2-dichloroethane (2 mL) in a 2-5 mL capacity microwave tube, is added acetic acid (0.06 mL, 1.0 mmol) and sodium triacetoxyborohydride (178 mg, 0.84 mmol). The tube is sealed with a septum and the mixture is heated at 140° C. for 10 minutes in a Biotage Initiator microwave. After cooling to room temperature, the solvents are removed under reduced pressure and the residue is purified by chromatography on a pre-packed reverse phase column. [MH+428.45].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08273900B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-6ae6e6217bf0450495043179fc70d506 |
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| Source note | uspto-grants-2012_09 |
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