Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | HCID 90407760 | HCID 90407760 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 90408074 | HCID 90408074 | 56% |
Reaction Steps
To a mixture of 2-[1-[2-(2-ethoxyphenyl)ethyl]imidazol-4-yl]pyridine-4-carbonitrile (1 eq) and NH4Cl (10 eq) in DMF was added NaN3 at rt, then stirred for 2 hr at 110° C. in a microwave oven, LC/MS showed the reaction was completed, acidified to PH=3-4 by conc. HCl, stirred for 1 hr, then adjusted to PH=7-8 by NaOH, concentrated and purified by HPLC to give the title compound (56%). 1H NMR (400 MHz, DMSO): δ 1.36 (3H, t, J=6.4 Hz), 3.06-3.09 (2H, m), 4.02-4.03 (2H, m), 4.25-4.29 (2H, m), 6.82-7.19 (4H, m), 7.69 (1H, s), 7.76-7.81 (2H, m), 8.47 (1H, s), 8.61 (1H, d, J=6.0 Hz). [M+H] Calc'd for C19H19N7O, 362. Found, 362.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09133166B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-9afd03e18746456fa9f0d63cb31bbb22 |
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| Source note | uspto-grants-2015_09 |
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