Acrylic Acid → HCID 57801513, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1.[C:25]([OH:29])(=[O:28])[CH:26]=[CH2:27]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][N:12]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[CH2:27][CH2:26][C:25]([OH:29])=[O:28]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of [1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-amine (see Example 6), (113 mg, 0.31 mmol), acrylic acid (23 mg, 0.33 mmol) and benzene (4 mL) was heated to reflux for 14 h. The solvent was evaporated in vacuo to afford crude 3-[[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-amino]-propionic acid. To a mixture of this acid (135 mg, 0.31 mmol), isonipecotamide (44 mg, 0.35 mmol), 1-hydroxybenzotriazole (45 mg, 0.33 mmol) and CH2Cl2 (1 mL) at 0° C. was added a solution of dicyclohexylcarbodiimide (68 mg, 0.33 mmol) in CH2Cl2 (0.5 mL). The mixture was stirred at ambient temperature for 14 h and then concentrated in vacuo. The residue was purified by column chromatography (silica gel, 20:1 to 10:1 CH2Cl2/MeOH) to provide the title compound (86 mg, 51%) as a white solid: ESI MS m/z 546 [C27H30Cl2FN5O2+H]+.