HCID 66859549, compound → (Z)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-9-(2,4-dichlorophenyl)-8,9-dihydro-5H-[1,2,4]triazolo[1,5-a]azepin-2-amine

Participants

Reaction Steps

1-Allyl-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-5-(1-(2,4-dichlorophenyl)but-3-enyl)-1H-1,2,4-triazol-3-amine (450 mg, 0.094 mmol) was subjected to a ring closing metathesis procedure analogous to Step C of Example 1 (160° C., 15 min, 25 mol % Hoveyda-Grubbs Catalyst 2nd Generation) to afford (Z)—N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-9-(2,4-dichlorophenyl)-8,9-dihydro-5H-[1,2,4]triazolo[1,5-a]azepin-2-amine (64.5 mg, 15% yield) as a dark brown solid. LC-MS (M+H)+=501.1. 1H NMR (500 MHz, chloroform-d) δ ppm 7.51 (d, J=1.53 Hz, 1 H) 7.45 (d, J=2.14 Hz, 1 H) 7.39 (d, J=2.14 Hz, 1 H) 7.25-7.30 (m, 1 H) 7.21-7.25 (m, 1 H) 7.09 (d, J=−8.55 Hz, 1 H) 7.02 (d, J=1.53 Hz, 1 H) 6.80 (dd, J=8.39, 2.29 Hz, 1 H) 6.63 (s, 1 H) 5.99-6.10 (m, 2 H) 4.81-5.01 (m, 3 H) 3.79 (s, 3 H) 2.78-2.97 (m, 1 H) 2.58-2.78 (m, 1 H).

Provenance & Evidence