2-(1H-Imidazol-2-yl)-1,3-thiazole → 3-ethyl-2-{[2-(1,3-thiazol-2-yl)-1H-imidazol-1-yl]methyl}-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine
Reaction equation
C([N:3]1[C:11]2[CH:10]=[C:9]([C:12]([F:15])([F:14])[F:13])[N:8]=[CH:7][C:6]=2[N:5]=[C:4]1[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]1[S:23][CH:24]=[CH:25][N:26]=1)C.Cl[CH2:28][C:29]1N(CC)C2C=NC(C(F)(F)F)=CC=2N=1.N1C=CN=C1C1SC=CN=1>>[CH2:28]([N:5]1[C:6]2[CH:7]=[N:8][C:9]([C:12]([F:14])([F:15])[F:13])=[CH:10][C:11]=2[N:3]=[C:4]1[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]1[S:23][CH:24]=[CH:25][N:26]=1)[CH3:29]Participants
4
Procedure
As described previously for the preparation of 1-Ethyl-2-(2-thiazol-2-yl-imidazol-1-ylmethyl)-6-trifluoromethyl-1H-imidazo[4,5-c]pyridine, nucleophilic displacement of the 2-chloromethyl-3-ethyl-6-trifluoromethyl-3H-imidazo[4,5-c]pyridine with the same 2-(1H-imidazol-2-yl)-thiazole followed by usual work provides 3-ethyl-2-{[2-(1,3-thiazol-2-yl)-1H-imidazol-1-yl]methyl}-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine. 1H NMR (CD3OD) δ 9.02 (s, 1H), 7.89 (s, 1H), 7.70 (d, J=3 Hz, 1H), 7.52 (d, J=3.3 Hz, 1H), 7.46 (d, J=1.5 Hz, 1H), 7.19 (d, J=1.5 Hz, 1H), 6.29 (s, 2H), 4.56 (q, J=7.5 Hz, 2H), 1.52 (t, J=7.5 Hz, 3H) m/z 379 [M+1]
Sources & evidence
- ORD record
- ord-92254c67518248d78a53c5d4f9b831d0
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06916819B2
Reaction notes
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