[1-(3-Chloro-4-cyano-2-methylphenyl)-3-methyl-2,5-dioxoimidazolidin-4-ylmethyl]carbamic Acid tert-butyl Ester → HCID 69516096, compound
Reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]1[C:13](=[O:14])[N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[C:17]([Cl:23])[C:16]=2[CH3:24])[C:11](=[O:25])[N:10]1[CH3:26])(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:7][CH2:8][CH:9]1[C:13](=[O:14])[N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[C:17]([Cl:23])[C:16]=2[CH3:24])[C:11](=[O:25])[N:10]1[CH3:26]Participants
4
Procedure
A solution of the N-Boc-protected amine 13B (260 mg, 0.662 mmol) in CH2Cl2 (3 mL) and TFA (3 mL) was stirred at rt for 1.5 h. The solution was then concentrated under reduced pressure to afford the title compound (349 mg) as a brown foam as the TFA salt. 1H NMR (CD3OD) δ 2.32, 2.33 (s, 3H), 3.07, 3.09 (s, 3H), 3.49-3.64 (m, 2H), 4.50-4.52 (m, 1H), 4.63-4.65 (m, 1H), 7.46 (d, J=8.3 Hz, 1H), 7.79, 7.80 (d, J=8.23 Hz, 1H); HPLC a) column: Phenominex ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 1.50, 1.65 min retention time; HPLC b) column: Shimadzu Shim-Pack VP-ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 0.90, 1.11 min retention time (90%); MS (ES) m/z 293 [M+H]+.