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]=1Participants
Reactant 3
Product 1
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
Sources & evidence
- ORD record
- ord-0fa707c73df64491a65a9d9457bd2dae
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221797B2
Reaction notes
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