Nitric Acid → HCID 86652704, compound
Reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].[N+:12]([O-:15])([OH:14])=[O:13].[C:16]([NH-:18])#[N:17]>C(O)C>[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].[N+:12]([O-:15])([OH:14])=[O:13].[NH2:17][C:16]([NH2:4])=[NH:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The synthesis of WBZ4, as shown in scheme 3 below, begins with treatment of 2-methyl-5-nitroaniline (1) with 65% nitric acid in ethanol followed by the addition of cyanoamide to give the corresponding 2-methyl-5-nitroaniline-guanidine nitrate (2). Once completed, nicotinate (3) was first treated with sodium hydrate and refluxed with ethyl acetate to form methyl 6-methylnicotinylacetate. The intermediate acetate was then hydrolyzed to form 3-Acetyl-6-methylpyridine (4). The product (4) was treated with methyl dimethoxyforamide to give 3-dimethylamino-1-(3-(6-methyl-pyridyl)-2-propene-1-one (5). The nitrate salt (2) is treated with (5) and sodium hydroxide in refluxing isopropanol to give N-(2-Methyl-5-nitrophenyl)-4-(3-(6-methyl-pyridyl))-2-pyrimidine-amine (6) which is subsequently hydrogenated with 10% palladium on carbon to give N-(2-Methyl-5-aminophenyl)-4-(3-6-methyl-pyridyl)-2-pyrimidine-amine (7). The WBZ4 synthesis will consist of the reaction of α-chloro-p-toluylic acid (8) with 4-methyl-piperazine in ethanol followed by treatment with concentrated HCl to give the corresponding dihydrochloride 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid (9) which is subsequently treated with thionyl chloride to give the corresponding acid chloride dihydrochloride (10). Subsequent condensation with N-(2-Methyl-5-aminophenyl)-4-(3-(6-methyl)-pyridyl)-2-pyrimidine-amine (7) in pyridine affords Formula 5 (WBZ4).
Workup
- customThe synthesis of WBZ4
Sources & evidence
- ORD record
- ord-5782129cebfa48bea3f38a3942b0dad7
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466154B2
Reaction notes
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