Methylamine → methyl-6-(4-(3-(methylamino)propoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile
Reaction equation
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20]([C:22]#[N:23])[C:19]3[N:24]=[CH:25][N:26]([CH3:27])[C:18]=3[CH:17]=2)=[CH:12][C:11]=1[C:28]([F:31])([F:30])[F:29])(=O)=O.[CH3:32][NH2:33].C(Cl)Cl.C(Cl)Cl.CO>C1COCC1.CN1C(=O)CCC1.CO>[CH3:27][N:26]1[C:18]2[CH:17]=[C:16]([C:13]3[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][CH2:6][NH:33][CH3:32])=[C:11]([C:28]([F:31])([F:29])[F:30])[CH:12]=3)[N:21]=[C:20]([C:22]#[N:23])[C:19]=2[N:24]=[CH:25]1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 3-(4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)propyl methanesulfonate (1.5 g) and methylamine in THF (2M, 8.25 ml) in NMP (12 ml) was heated at 100° C. under microwave conditions for 30 minutes. The mixture was then columned on silica gel using DCM-DCM-MeOH (19:1) then MeOH-2M ammonia in MeOH as eluant to give the expected product (757 mg). 1H NMR (CD3OD) δ: 8.43 (s, 1H), 8.31-8.40 (m, 3H), 7.31 (d, 1H), 4.26 (t, 2H), 4.02 (s, 3H), 2.80 (t, 2H), 2.41 (s, 3H), 2.06 (quin, 2H). MS m/z 390 (M+H).
Sources & evidence
- ORD record
- ord-9b7f5cf1ace94bffa73441ce5b4597e6
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026236B2
Reaction notes
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