Ethanol → 3-(3-Chloro-phenyl)-5-{2-[3-cyclopropyl-2-(4-methoxy-phenyl)-3h-imidazol-4-yl]-ethyl}-[1,2,4]oxadiazole

HRID 732135Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[N:10][OH:11])[NH2:9])[CH:5]=[CH:6][CH:7]=1.C(O[C:15](=O)[CH2:16][CH2:17][C:18]1[N:19]([CH:31]2[CH2:33][CH2:32]2)[C:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[N:21][CH:22]=1)C.CC(C)([O-])C.[Na+].CCO>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:15]([CH2:16][CH2:17][C:18]3[N:19]([CH:31]4[CH2:33][CH2:32]4)[C:20]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)=[N:21][CH:22]=3)[O:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3-chloro-N′-hydroxybenzenecarboximidamide (54.3 mg, 0.32 mmol), 3-[3-cyclopropyl-2-(4-methoxy-phenyl)-3H-imidazol-4-yl]-propionic acidethyl ester (100 mg, 0.32 mmol) and sodium-tert-butoxide (30.6 mg, 0.32 mmol) were mixed with EtOH (1 ml) and toluene (1 ml), followed by stirring at 100° C. for 24 h. The mixture was then concentrated, in-vacuo, and the residue was purified via column chromatography using 50% EA in hex. and then triturated with Et2O to isolate the title compound (27 mg). 1H-NMR: 8.1 (m, 1H), 7.97 (dd, 1H), 7.64 (d, 2H), 7.47 (m, 2H), 6.96 (d, 2H), 6.88 (s, 1H), 3.87 (s, 3H), 3.37 (m, 4H), 3.24 (m, 1H), 1.06 (m 2H), 0.68 (m, 2H).

Workup

concentrationThe mixture was then concentrated
customin-vacuo, and the residue was purified via column chromatography
customand then triturated with Et2O

Sources & evidence

ORD record: ord-824e0739fe424bfca98a5da87d2b5497
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585881B2

Reaction notes

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