Benzoyl chloride → HCID 61710259, compound
Reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.[N:29]1([CH2:35][CH2:36][CH2:37][NH2:38])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>>[NH2:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([NH:38][CH2:37][CH2:36][CH2:35][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:6])=[C:2]([F:1])[CH:10]=1Participants
Procedure
Anilines with other sidechains will be readily prepared by a person having ordinary skill in the art having regard to that skill and this disclosure, and will be usable in the syntheses of Reaction Scheme 4. For example, diethyl (4-nitrobenzyl)phosphonate was reacted in a Wittig reaction with pyridin-3-carboxaldehyde and the resulting 3-(4-nitrostyryl)pyridine hydrogenated to give 4-[2-(pyridin-3-yl)ethyl]benzenamine, used to synthesize compound 99A, and the anilines used to synthesize compounds 97A and 98A were similarly prepared; 4-nitrobenzaldehyde was reacted with glyoxal and ammonia to give 2-(4-nitrophenyl)-1H-imidazole, which was N-methylated with methyl iodide and then reduced with stannous chloride to give 4-(1-methyl-1H-imidazol-2-yl)benzenamine, used to synthesize compound 106A; 2-fluoro-4-nitrobenzoic acid was converted to the corresponding benzoyl chloride with oxalyl chloride, then reacted with 3-(morpholin-4-yl)propan-1-amine and reduced to give 4-amino-2-fluoro-N-[3-(morpholin-4-yl)propyl]benzamide, used to synthesize compound 50A; and 4-nitrobenzenesulfonyl chloride was reacted with 2-(morpholin-4-yl)ethan-1-amine and then reduced with stannous chloride to give 4-amino-N[2-(morpholin-4-yl)ethyl]benzenesulfonamide, used to synthesize compound 128A.
Sources & evidence
- ORD record
- ord-39aa10fee70048d6ad17d5315ad77445
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129396B2
Reaction notes
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