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

HRID 1190167Notes

Reaction equation

HRID 1190167 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

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 58994521HCID 58994521, compoundHCID 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

Sources & evidence

ORD record
ord-16f75efcfcd54403b1b17661aedb9e72
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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