5-ethoxy-6-ethyl-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-1H-benzoimidazole → 3-(5-ethoxy-6-ethyl-1H-benzoimidazol-2-yl)-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-ylamine
Reaction equation
[CH2:1]([O:3][C:4]1[C:26]([CH2:27][CH3:28])=[CH:25][C:7]2[NH:8][C:9]([C:11]3[C:15]([N+:16]([O-])=O)=[CH:14][N:13]([CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][O:20]4)[N:12]=3)=[N:10][C:6]=2[CH:5]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]1[C:26]([CH2:27][CH3:28])=[CH:25][C:7]2[NH:8][C:9]([C:11]3[C:15]([NH2:16])=[CH:14][N:13]([CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][O:20]4)[N:12]=3)=[N:10][C:6]=2[CH:5]=1)[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 5-ethoxy-6-ethyl-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-1H-benzoimidazole [0.8 g, Reference Example 50(a)] in ethanol (100 mL) was treated with palladium on carbon (0.1 g, 10%) and mixture was hydrogenated at atmospheric pressure (balloon) for 4 days. The catalyst was filtered off, the filtrate was evaporated and the residue was chromatographed on silica gel (ethyl acetate with gradient of 0-10% methanol) to give 3-(5-ethoxy-6-ethyl-1H-benzoimidazol-2-yl)-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-ylamine (0.3 g) as a solid. LC-MS (Method E): RT=2.15 minutes, 356 (M+H)+.
Workup
- filtrationThe catalyst was filtered off
- customthe filtrate was evaporated
- customthe residue was chromatographed on silica gel (ethyl acetate with gradient of 0-10% methanol)
Sources & evidence
- ORD record
- ord-f041a8f173e4405e99f32a927c6560be
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288425B2
Reaction notes
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