Imidazole → HCID 54674967, compound

HRID 2402754Notes

Reaction equation

BrC1C=CC(S(O[C@H:12]2[C@@H:19]3[C@@H:15]([CH2:16][N:17]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]=4)[CH2:18]3)[CH2:14][CH2:13]2)(=O)=O)=CC=1.[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1>C1(C)C=CC=CC=1>[N:30]1([C@@H:12]2[C@@H:19]3[C@@H:15]([CH2:16][N:17]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]=4)[CH2:18]3)[CH2:14][CH2:13]2)[CH:34]=[CH:33][N:32]=[CH:31]1

Participants

Conditions

Temperature: 90 °C

Procedure

A 4 mL vial was charged with (3aR,4R,6aS)-2-[6-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl 4-bromobenzenesulfonate (100 mg, 0.204 mmol) from Example 39 and 1H-imidazole (55.4 mg, 0.814 mmol) in toluene (0.5 mL). The reaction was heated at 90° C. for 24 hours, and then the reaction mixture was concentrated. The residue was purified by silica gel chromatography using 0-4% methanol (2 N ammonia)/dichloromethane as eluent to give the title compound: 1H NMR (400 MHz, pyridine-d5) δ ppm 7.98 (s, 1H), 7.55 (d, J=8.1, 1H), 7.43 (s, 1H), 7.28 (t, J=1.2, 1H), 7.03 (d, J=7.3, 1H), 6.53 (d, J=8.6, 1H), 4.29 (dt, J=8.5, 6.6, 1H), 3.57-3.44 (m, 2H), 3.39 (dd, J=11.2, 7.2, 1H), 3.27 (dd, J=10.9, 4.2, 1H), 2.89-2.72 (m, 2H), 2.12 (dtd, J=11.3, 7.1, 3.8, 1H), 2.03-1.94 (m, 1H), 1.87 (ddd, J=17.3, 12.6, 8.6, 1H), 1.49-1.32 (m, 1H); MS (ESI+) m/z 323 (M+H)+.

Workup

concentrationthe reaction mixture was concentrated
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-b472f88be7a643b58dd4b01c184b4012
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796470B2

Reaction notes

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