Trifluoroacetic acid → HCID 66970554, compound
Reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[CH:9][N:8]([C:11]3[N:16]=[C:15]4[N:17]([C@@H:28]([C:30]5[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=5)[CH3:29])[C:18](=[O:27])[N:19](C(OC(C)(C)C)=O)[C:14]4=[CH:13][CH:12]=3)[C:7]=2[CH:36]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:27]=[C:18]1[N:17]([C@@H:28]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH3:29])[C:15]2=[N:16][C:11]([N:8]3[C:7]4[CH:36]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=4[N:10]=[CH:9]3)=[CH:12][CH:13]=[C:14]2[NH:19]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of tert-butyl 5-(6-cyano-1H-benzo[d]imidazol-1-yl)-2-oxo-3-((R)-1-(pyridin-3-yl)ethyl)-2,3-dihydroimidazo[4,5-b]pyridine-1-carboxylate (72) (57 mg) in methylene chloride (1 mL) was treated with TFA (1 mL) for one hour. The mixture was concentrated and the resulting TFA salt was converted to the HCl salt by dissolving it in 5 mL EtOH and adding 0.5 mL of conc. HCl, then concentrating the solution in vacuo. The process was repeated and the resulting residue was dissolved in a minimum amount of methanol and triturated with the addition of ethyl ether. After 3 triturations, 3-(2-oxo-3-((R)-1-(pyridin-3-yl)ethyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)-3H-benzo[d]imidazole-5-carbonitrile (73) HCl salt (39 mg) was isolated as a tan colored solid: 1H-NMR (CD3OD) δ 9.9 (br s, 1H), 9.2 (s, 1H), 9.0 (m, 2H), 8.5 (s, 1H), 8.3 (m, 1H), 8.2 (m, 1H), 8.1 (d, 1H), 7.9 (d, 1H), 7.8 (d, 1H), 6.3 (q, 1H), 2.3 (d, 3H).