Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 4-Fluorobenzylic alcohol | HCID 68022 | — |
| Reactant | Triacetoxyperiodinane | HCID 159087 | — |
| Reactant | Cyano-borohydride | HCID 498716 | — |
| Reactant | N-(7-chloroquinolin-4-yl)cyclohexane-1,4-diamine | HCID 18391686 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178505712 | HCID 178505712 | — |
Reaction Steps
To 4-fluorobenzyl alcohol (9.2 mg, 0.073 mmol) was added Dess-Martin periodinane (31.0 mg, 0.073 mmol) in dichloromethane (2 mL). The mixture was stirred at room temperature for 0.5 hour and was added to a mixture of N-(7-chloroquinolin-4-yl)-cyclohexane-1,4-diamine (20 mg, 0.073 mmol), acetic acid (0.008 mg, 0.13 mmol) and MP-cyanoborohydride (51 mg, 0.219 mmol, Argonaut Technologies) in dichloromethane (5 mL). The mixture was stirred at room temperature for 18 hours, filtered and concentrated under reduced pressure to provide the τιτλεδ compound. MS(ESI) m/e 384 (M+H)+; 1H NMR (500 MHz, DMSO-D6) δ ppm 8.91 (br.s, 2 H), 8.75 (d, 1 H), 8.61 (d, 1 H), 7.97 (d, 1 H), 7.81 (dd, 1 H), 7.52 (dd, 1 H), 7.42 (d, 1 H), 7.37 (d, 1 H), 7.29 (td, 1 H), 4.25 (br.s, 2 H), 4.09 (br.s, 2 H), 1.76-2.13 (m, 8 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06818772B2 |
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| Source dataset | uspto-grants-2004_11 |
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| ORD ID | ord-f36bd8de86c74affacf0bcca32ea8290 |
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| Source note | uspto-grants-2004_11 |
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