1,1'-Carbonyldiimidazole → N-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-N-(4-fluorophenyl)-1H-imidazole-1-carboxamide

HRID 445377Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])=[CH:4][CH:3]=1.[C:22](N1C=CN=C1)([N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1)=[O:23]>C1COCC1>[O:20]=[C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:21])[N:11]1[CH2:10][CH2:9][N:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:22]([N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1)=[O:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To a 50 mL round-bottomed flask was added 2-(2-(4-fluorophenylamino)ethyl)-isoindoline-1,3-dione (204 mg, 718 μmol, from step 1), 1,1′-carbonyldiimidazole (175 mg, 1076 μmol, Aldrich), THF (2 mL). The reaction mixture was stirred at 80° C. for 24 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 80% EtOAc/hexanes to give N-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-N-(4-fluorophenyl)-1H-imidazole-1-carboxamide. MS (ESI pos. ion) m/z: 379 (M+1).

Workup

customThe solvent was removed in vacuo
customthe residue was purified by silica gel chromatography
washeluting with 80% EtOAc/hexanes

Sources & evidence

ORD record: ord-72b84fa3fe60428681837eaaeae6beb1
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476297B2

Reaction notes

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