Cesium carbonate → 4-Allyl-5-(4-chlorophenyl)-2-{[1-(2,6-dichlorobenzyl)-4-nitro-1H-imidazol-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714720Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][CH:15]=[CH2:16])[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.Cl[CH2:18][C:19]1[N:20]([CH2:27][C:28]2[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:35])[CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[N:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:14]([N:9]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[N:12][N:11]([CH2:18][C:19]2[N:20]([CH2:27][C:28]3[C:29]([Cl:35])=[CH:30][CH:31]=[CH:32][C:33]=3[Cl:34])[CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[N:23]=2)[C:10]1=[O:13])[CH:15]=[CH2:16]

Participants

Conditions

Temperature: 80 °C

Procedure

110 mg (0.47 mmol) of the compound from Example 12A were dissolved in 10 ml of DMF, and 150 mg (0.47 mmol) of the compound from Example 41A and 229 mg (0.70 mmol) of cesium carbonate were added. The mixture was stirred at 80° C. for 16 h. After cooling to RT, the reaction mixture was added to about 25 ml of ice-water and stirred for 10 min. This resulted in the formation of a precipitate which was filtered off with suction and washed with water. The solid was dried under high vacuum. This gave 120 mg (44% of theory) of the target compound of a purity of 90%.

Workup

temperatureAfter cooling to RT
stirringstirred for 10 min
customThis resulted in the formation of a precipitate which
filtrationwas filtered off with suction
washwashed with water
customThe solid was dried under high vacuum

Sources & evidence

ORD record: ord-c83edcda6f7a4a998fd4583f8eb83acd
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187466B2

Reaction notes

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