Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | (4-{4-[6-(6-Trifluoromethyl-pyridin-3-ylamino)-pyridazin-3-yl]-phenyl}-cyclohexyl)-acetonitrile | HCID 66615964 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 57899092 | HCID 57899092 | — |
Reaction Steps
To a mixture of (4-{4-[6-(6-Trifluoromethyl-pyridin-3-ylamino)-pyridazin-3-yl]-phenyl}-cyclohexyl)-acetonitrile (0.12 g, 0.29 mmol, 1.0 equiv) in 3 Ml DMF was added sodium azide (0.057 g, 0.88 mmol, 3.0 equiv), followed by solid ammonium chloride (0.062 g, 4.0 equiv). The reaction was heated to 140° C. over the weekend. The cooled reaction mixture was diluted with 10 Ml water and then acidified to Ph 4-5. The precipitate was filtered to afford the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 103-1.16 (m, 2 H) 1.33-1.45 (m, 2 H) 1.73 (t, J=14.27 Hz, 5 H) 2.60-2.68 (m, 3 H) 7.27 (dd, J=17.94, 8.84 Hz, 3 H) 7.79 (d,J=8.84 Hz, 1 H) 7.86-7.95 (m, 2 H) 8.01 (d, J=9.09 Hz, 1 H) 8.63 (dd, J=8.59, 1.77 Hz, 1 H) 8.87 (d, J=2.27 Hz, 1 H) 9.99 (s, 1 H); (M+H)+ 481.7.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08912208B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-50dcbb9e0a79461aa480474be2f5b959 |
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| Source note | uspto-grants-2014_12 |
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