4-Cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylic acid → HCID 86609181, compound
Reaction equation
[N:1]1([C:7]2[N:8]=[N:9][CH:10]=[CH:11][C:12]=2[NH2:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([C:16]1[N:17]=[C:18]([C:29]([OH:31])=O)[N:19]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:20]=1)#N.[K+].[C:33](C1N=C(C([O-])=O)N(COCC[Si](C)(C)C)C=1)#[N:34]>>[N:1]1([C:7]2[N:8]=[N:9][CH:10]=[CH:11][C:12]=2[NH:13][C:29]([C:18]2[N:19]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:26])([CH3:27])[CH3:28])[C:20]([C:33]#[N:34])=[CH:16][N:17]=2)=[O:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
4
Procedure
3-Piperidin-1-yl-pyridazin-4-ylamine (as prepared in above step) was coupled with 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid, potassium salt (as prepared in Example 11, step (d)), as described in Example 42, step (c) to afford 5-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (3-piperidin-1-yl-pyridazin-4-yl)-amide which was subjected to SEM deprotection as described in Example 47, step (d) to afford the title compound. 1H-NMR (DMSO-d6; 400 MHz): δ 9.79 (br s, 1H), 9.03 (d, 1H, J=4 Hz), 8.50 (s, 1H), 8.43 (d, 1H, J=4 Hz), 3.21 (m, 4H), 1.71-1.86 (m, 6H); Mass spectrum (ESI, m/z): Calcd. for C14H15N7O, 298.1 (M+H), found 298.1.
Sources & evidence
- ORD record
- ord-29e60936022b46c5bebc6c9ddb326dd4
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790724B2
Reaction notes
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