4-(Trifluoromethyl)benzylamine → 3-Chloro-4-hydroxybenzoic Acid {2-Methoxy-4-[2-(4-Trifluoromethylbenzylamino)ethoxy]-benzylidene}hydrazide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([NH:7][NH2:8])=[O:6].Br[CH2:14][CH2:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[C:19]([O:25][CH3:26])[CH:18]=1.[F:27][C:28]([F:38])([F:37])[C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1>>[CH3:26][O:25][C:19]1[CH:18]=[C:17]([O:16][CH2:15][CH2:14][NH:34][CH2:33][C:32]2[CH:31]=[CH:30][C:29]([C:28]([F:27])([F:37])[F:38])=[CH:36][CH:35]=2)[CH:24]=[CH:23][C:20]=1[CH:21]=[N:8][NH:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][C:11]([OH:12])=[C:2]([Cl:1])[CH:3]=1Participants
4
Procedure
This compound was prepared analogously to the compound described in the previous example starting from resin bound 3-chloro-4-hydroxybenzoic acid hydrazide (resin—[building block 1]) (2 g, ˜2 mmoles), 4-(2-bromoethoxy)-2-methoxybenzaldehyde ([building block 2]) (0.73 g, 1.5 equivs.), and 4-trifluoromethylbenzylamine ([building block 3]) (3.3 g, 10 equivs.). After cleavage with 50% trifluoroacetic acid, the residue (1 g) was purified by column chromatography on silica gel (20 g) eluting with a mixture of 25% aq. ammonia, ethanol and dichloromethane (1:9:115). This afforded 130 mg of the title compound.
Workup
- customThis compound was prepared analogously to the compound
- customAfter cleavage with 50% trifluoroacetic acid, the residue (1 g) was purified by column chromatography on silica gel (20 g)
- washeluting with a mixture of 25% aq. ammonia, ethanol and dichloromethane (1:9:115)
Sources & evidence
- ORD record
- ord-d0683c970cfb4293abd525946f64dd45
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06613942B1
Reaction notes
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