Phosgene → 1-Cyclopropyl-3-[3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-3h-imidazol-4-yl]-urea

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Reaction Steps

In the first step a modified Mitsunobu reaction employing 5-nitro-1H-imidazole (CAS #3034-38-6) can be preformed as described in Example 1. The resulting 5-nitro-1(1,2,3,4-tetrahydro-naphthalen-1-yl)-1H-imidazole, can then be reduced via the employment of palladium on carbon under a hydrogen atmosphere. The resulting amine can undergo treatment with phosgene followed by the addition of cyclopropylamine to afford 1-cyclopropyl-3-[3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazol-4-yl]-urea; MS: (ESI) m/z 297.1 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 0.46-0.57 (m, 2 H), 0.68-0.77 (m, 2 H), 1.78-2.29 (m, 4 H), 2.49-2.60 (m, 1 H), 2.79-3.01 (m, 2 H), 5.17-5.31 (m, 1 H), 5.34-5.43 (m, 1 H), 6.33-6.43 (m, 1 H), 6.85 (d, J=7.6 Hz, 1 H), 7.01 (s, 1 H), 7.13 (t, J=7.5 Hz, 1 H), 7.17-7.26 (m, 3 H).

Provenance & Evidence