5-methyl-4-(methylamino)methyl-1-triphenylmethyl-1H-imidazole → HCID 19900737, compound
Reaction equation
[CH3:1][C:2]1[N:6]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[N:4][C:3]=1[CH2:26][NH:27]C.[CH3:29][CH:30]1[CH2:39][CH2:38][C:37]2[C:32]3=[C:33]([C:40]([C:42]([OH:44])=O)=[CH:41][N:31]13)[CH:34]=[CH:35][CH:36]=2>C(#N)C>[CH3:1][C:2]1[N:6]([C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[N:4][C:3]=1[CH2:26][NH:27][C:42]([C:40]1[C:33]2=[C:32]3[C:37](=[CH:36][CH:35]=[CH:34]2)[CH2:38][CH2:39][CH:30]([CH3:29])[N:31]3[CH:41]=1)=[O:44]Participants
4
Procedure
A mixture of 3.4 g (9.3 mmol) of 5-methyl-4-(methylamino) methyl-1-triphenylmethyl-1H-imidazole, 2.0 g (9.3 mmol) of 4-methyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid, and 2.06 g (10 mmol) of N,N-dicyclohexylcarbodiimide in 100 ml of acetonitrile was stirred for 12 hours under nitrogen. The precipitate was sucked off and the filtrate was evaporated in vacuo. The residue was dissolved in ethylacetate and washed with 2 N sodium hydroxide and saturated saline respectively, and then evaporated in vacuo. The residue was chromatographed on silicagel using methylene chloride/methanol (95/5) as an eluent. After evaporating the desired fractions 3.6 g of N-methyl, N-[(5-methyl-1-triphenylmethyl-1H-imidazol-4-yl)methyl]-4-methyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxamide were obtained.