4-Methoxy-3-(2-methylpropoxy)benzaldehyde → 6-[1-(3-Isobutoxy-4-methoxy-benzyl)-piperidin-4-ylamino]-4-trifluoromethyl-nicotinamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=3)[CH2:10][CH2:9]2)=[CH:5][C:4]=1[O:30][CH2:31][CH2:32][CH3:33].Cl.Cl.[CH3:36]OC(=O)C1C(C(F)(F)F)=CC(NC2CCNCC2)=NC=1.C(OC1C=C(C=CC=1OC)C=O)C(C)C>>[CH2:31]([O:30][C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][C:3]=1[O:2][CH3:1])[CH2:7][N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=2)[CH2:12][CH2:13]1)[CH:32]([CH3:36])[CH3:33]Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared in analogy to the synthesis of 6-[1-(4-methoxy-3-propoxy-benzyl)-piperidin-4-ylamino]-4-trifluoromethyl-nicotinamide (example 197) from 6-(piperidin-4-ylamino)-4-trifluoromethyl-nicotinic acid methyl ester dihydrochloride (intermediate B7) and 3-isobutoxy-4-methoxy-benzaldehyde (intermediate E12) in a yield of 15.1 mg (21%). MS (ISP): 482.4 [M+H]+.
Sources & evidence
- ORD record
- ord-13cbdcd5d6d042b183aa20f0b53a3bb4
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026255B2
Reaction notes
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