3-Aminopyridine → 6-(4-Ethoxy-3-trifluoromethyl-phenyl)-2-(pyridin-3-ylaminomethyl)-1h-imidazo[4,5-c]pyridine-4-carbonitrile
Reaction equation
Cl[CH2:2][C:3]1[NH:4][C:5]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[C:13]([C:20]([F:23])([F:22])[F:21])[CH:12]=3)[N:8]=[C:7]([C:24]#[N:25])[C:6]=2[N:26]=1.[NH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1>>[CH2:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:8]=[C:7]([C:24]#[N:25])[C:6]3[N:26]=[C:3]([CH2:2][NH:27][C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)[NH:4][C:5]=3[CH:10]=2)=[CH:12][C:13]=1[C:20]([F:23])([F:22])[F:21])[CH3:19]Participants
3
Procedure
A solution of 2-chloromethyl-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5,c]pyridine-4-carbonitrile (20 mg, 0.052 mmol), diisoproplylethylamine (28.4 uL,0.16 mmol) and 3-aminopyridine (9.8 mg, 0.1 mmol) dimethylsulfoxide (500 μL) was heated in the Creator microwave at 120° C. for 5 minutes. The mixture was filtered and purified by preparative HPLC to afford the title compound. 1H NMR (MeOH) δ 8.3-8.2 (m, 5H), 7.76-7.74 (m, 2H), 7.27 (d, 1H), 6.07 (s, 2H) 4.23 (q, 2H) 1.45 (t, 3H) MS m/z 439.1 (m+1).
Workup
- filtrationThe mixture was filtered
- custompurified by preparative HPLC
Sources & evidence
- ORD record
- ord-cf8ab6b42913403f869412efb15560cf
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687515B2
Reaction notes
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