74150-02-0

Basic information

• Product Name: 6-(3,4-diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one
• Synonyms: 6-(3,4-diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one;6-(3,4-Diaminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone;PiMobendan N-1;3(2H)-Pyridazinone, 6-(3,4-diaMinophenyl)-4,5-dihydro-5-Methyl-;6-(3,4-Diaminophenyl)-5-methyl-4,5-dihydropyridazin
• CAS NO: 74150-02-0
• Molecular Formula: C₁₁H₁₄N₄O
• Molecular Weight: 218.26
• Product Categories: API
• Mol File: 74150-02-0.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Density: 1.43
• Storage Temp.: 2-8°C
• PKA: 13.67±0.60(Predicted)
• CAS DataBase Reference: 6-(3,4-diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(3,4-diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one(74150-02-0)
• EPA Substance Registry System: 6-(3,4-diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one(74150-02-0)

Safety Data

• Hazardous Substances Data: 74150-02-0(Hazardous Substances Data)

Usage

Uses

6-(3,4-Diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one is a reactant used in the synthesis of (6-Oxo-3-pyridazinyl)benzimidazoles as potent angiotensin II receptor antagonists.

Upstream product

• 81112-08-5 N-[4-(2-chloro-1-oxopropyl)phenyl]acetamide 
• 81937-39-5 2-ethoxycarbonyl-3-(4-acetamidobenzoyl)butyric acid ethyl ester 
• 63514-63-6 N-(4-(2-bromopropionyl)phenyl)acetamide 
• 120757-17-7 methyl 3-(4-acetaminobenzoyl)butyrate 
• 82923-97-5 3-methoxycarbonyl-2-methyl-propionic acid chloride 
• 103-84-4 Acetanilid 
• 36725-26-5 4-(4-acetamidophenyl)-3-methyl-4-oxobutanoic acid 
• 1338058-47-1 ethyl 4-(4-(benzylamino)-3-nitrophenyl)-3-methyl-4-oxo-butanoate 
• 85633-97-2 4-(4-benzylamino-3-nitro-phenyl)-3-methyl-4-oxo-butyric acid 
• 117397-88-3 6-(4-chloro-3-nitrophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one 
• 85633-96-1 3-methyl-4-oxo-4-(3'-nitro-4'-chloro-phenyl)-butyric acid 
• 104-88-1 4-chlorobenzaldehyde 
• 52240-25-2 4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid 
• 53012-96-7 4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile 

Downstream Products

• 118428-37-8 pimobendan 
• 109-52-4 valeric acid 

Relevant articles and documents

Synthesis method of pimobendan

The invention provides a synthesis method of pimobendan, and belongs to the technical field of pharmaceutical chemicals. The synthesis method comprises the following steps: (1) in an organic solvent,taking acetanilide and 2-chloropropionyl chloride as raw materials, generating a compound I under the action of a Lewis acid catalyst; (2) in acid anhydride, the compound I and nitric acid are subjected to a nitration reaction to produce a compound II; (3) carrying out nucleophilic substitution reaction on the compound II and diethyl malonate in a reaction reagent under the action of sodium methoxide, carrying out hydrolysis reaction in the reaction reagent under the action of sodium hydroxide, and regulating the pH value of the reaction system to 3-4 by using diluted hydrochloric acid to generate a compound III; (4) reacting the compound III with a decarboxylation reagent to generate a compound IV; (5) reacting the compound IV with hydrazine hydrate in a reaction solvent in the presence of a noble metal catalyst to generate a compound V; and (6) reacting the compound V with p-methoxybenzaldehyde in a reaction solvent under the action of a catalyst to generate pimobendan VI. The pimobendan prepared by the method is simple in preparation method and low in reagent toxicity and has excellent clinical curative effect and clinical safety.

Preparation method of key intermediate of Pimobendan

The invention discloses a preparation method of a key intermediate of Pimobendan. The method comprises steps as follows: (i) a compound I is synthesized; (ii) the compound I is subjected to nucleophilic substitution, and a compound II is produced; (iii) t

Synthesis of novel pyridazinonylbenzotriazoles

4-Chlorobenzaldehyde (1) was reacted with crotononitrile (2) in the presence of sodium cyanide yielding 4-(4-chlorophenyl)-3-methyl- 4-oxobutyronitrile (3) which on refluxing with concentrated HCl gave 4-(4-chlorophenyl)-3-methyl-4-oxobutyric acid (4). The latter, on treatment with fuming nitric acid, yielded 4-(4-chloro-3-nitrophenyl)-3-methyl-4-oxobutyric acid (5), which on treatment with hydrazine hydrate gave 6-(4-chloro-3-nitrophenyl)-5-methyl-4,5-dihydro-2H-pyridazine-3-one (6). Azidation and reduction of 6 with sodium azide gave the amino derivative 7 which on reductive alkylation gave 10(a-i) followed by reduction with commercially available sodium hydrogen sulphide solution gave the substituted diamine derivative 11(a-i). The compound 7 directly undergoes reduction with sodium hydrogen sulphide yielding (8). Finally, 8 and 11(a-i) was converted into the target compounds by diazotized-cyclization with sodium nitrite giving pyridazinonylbenzotriazoles 9 and 12(a-i).