Trifluoroacetic acid → 5-Chloro-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-morpholin-4-yl-ethyl)-phenyl]-amide hydrochloride

Reaction equation

[K+].[Cl:2][C:3]1[N:4]=[C:5]([C:16]([O-:18])=O)[N:6](COCC[Si](C)(C)C)[CH:7]=1.[C:19]1([C:25]2[CH:30]=[C:29]([CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[CH:28]=[CH:27][C:26]=2[NH2:39])[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=1.FC(F)(F)C(O)=O>>[ClH:2].[C:19]1([C:25]2[CH:30]=[C:29]([CH2:31][CH2:32][N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)[CH:28]=[CH:27][C:26]=2[NH:39][C:16]([C:5]2[NH:4][C:3]([Cl:2])=[CH:7][N:6]=2)=[O:18])[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 58994521HCID 58994521, compound

HCID 671881474-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate potassium salt

Product 1

HCID 248750705-Chloro-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-morpholin-4-yl-ethyl)-phenyl]-amide hydrochloride

Procedure

The title compound was prepared by coupling 4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate potassium salt and (as prepared in the previous step) and 2-cyclohex-1-enyl-4-(2-morpholin-4-yl-ethyl)-phenylamine (as prepared in Example 33, step (c)) according to the procedure in Example 34, step (c), followed by SEM deprotection according to the procedure in Example 34, step (d). The hydrochloride salt was prepared from the trifluoroacetic acid salt using a BioRad AG2-X8 resin, Cl− ion form. 1H-NMR (400 MHz, DMSO-d6): δ 13.73 (s, 1H), 10.52 (s, 1H), 9.58 (s, 1H), 8.00 (d, J=8.1 Hz, 1H), 7.53 (s, 1H), 7.20 (dd, J=8.1, 2.1 Hz, 1H), 7.14 (d, J=2.1 Hz, 1H), 5.77 (m, 1H), 4.00 (m, 2H), 3.74 (m, 2H), 3.57-3.41 (m, 4H), 3.19-2.93 (m, 4H), 2.27-2.13 (m, 4H), 1.79-1.65 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C22H27ClN4O2, 415.2 (M+H). found 415.1