Siguazodan

Base Information

• Chemical Name: Siguazodan
• CAS No.: 115344-47-3
• Molecular Formula: C₁₄H₁₆N₆O
• Molecular Weight: 284.321
• European Community (EC) Number: 634-221-4
• UNII: 5E4UI00UQJ
• DSSTox Substance ID: DTXSID0045202
• Nikkaji Number: J535.486B
• Wikipedia: Siguazodan
• Wikidata: Q15633560
• NCI Thesaurus Code: C74353
• ChEMBL ID: CHEMBL1256712
• Mol file: 115344-47-3.mol

Synonyms:2-cyano-1-methyl-3-(4-(methyl-6-oxo-1,4,5,6-tetrahydropyridazine-3-yl)phenyl)guanidine;siguazodan;SK and F 94836;SK and F-94836;SKF 94836

Chemical Property of Siguazodan

Chemical Property:

• Melting Point: 268-268.9 °C(lit.)
• Boiling Point: °Cat760mmHg
• PKA: 13.71±0.60(Predicted)
• Flash Point: °C
• PSA: 101.67000
• Density: 1.31g/cm³
• LogP: 1.37048
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >5 mg/mL, freely soluble
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 284.13855916
• Heavy Atom Count: 21
• Complexity: 495

Purity/Quality:

98%min ^*data from raw suppliers

Siguazodan ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(=O)NN=C1C2=CC=C(C=C2)NC(=NC)NC#N
• Uses: Siguazodan is a selective phosphodiesterase PDE III inhibitor and a potent inotropic agent.

Technology Process of Siguazodan

There total 13 articles about Siguazodan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

6-<4-(N'-cyano-S-methylisothioureido)phenyl>-5-methyl-4,5-dihydropyridazin-3(2H)-one (99591-85-2,123466-25-1) + methylamine (74-89-5) → 2 cyano 1 methyl 3 [4 (4 methyl 6 oxo 1,4,5,6 tetrahydro 3 pyridazinyl)phenyl]guanidine (115344-47-3)

Guidance literature:

In ethanol; for 2h; Heating;

DOI:10.1002/jhet.5570250615

Reference yield:

4-(4-acetamidophenyl)-4-oxobutanoic acid (5473-15-4) → 2 cyano 1 methyl 3 [4 (4 methyl 6 oxo 1,4,5,6 tetrahydro 3 pyridazinyl)phenyl]guanidine (115344-47-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 62 percent / H₂O / 1) room temperature, overnight, 2) steam bath, 2 h

2: conc. H₂SO₄ / 1 h / Heating

3: pyridine

4: H₂ / Raney Nickel / methanol / 0.33 h / 1034.3 Torr

5: 90 percent / hydrazine hydrate / ethanol; H₂O / 2 h / Heating

6: 76 percent / 1 M aq. HCl / 1.25 h / Heating

7: 65 percent / pyridine / 3.5 h / Heating

8: 72 percent / ethanol / 2 h / Heating

With pyridine; hydrogenchloride; sulfuric acid; hydrogen; hydrazine hydrate; nickel; In methanol; ethanol; water;

DOI:10.1002/jhet.5570250615

Reference yield:

3-(4-Acetylamino-benzoyl)-but-3-enoic acid methyl ester (120757-16-6) → 2 cyano 1 methyl 3 [4 (4 methyl 6 oxo 1,4,5,6 tetrahydro 3 pyridazinyl)phenyl]guanidine (115344-47-3)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Raney Nickel / methanol / 0.33 h / 1034.3 Torr

2: 90 percent / hydrazine hydrate / ethanol; H₂O / 2 h / Heating

3: 76 percent / 1 M aq. HCl / 1.25 h / Heating

4: 65 percent / pyridine / 3.5 h / Heating

5: 72 percent / ethanol / 2 h / Heating

With pyridine; hydrogenchloride; hydrogen; hydrazine hydrate; nickel; In methanol; ethanol; water;

DOI:10.1002/jhet.5570250615

upstream raw materials:

6-<4-(N'-cyano-S-methylisothioureido)phenyl>-5-methyl-4,5-dihydropyridazin-3(2H)-one

methylamine

N-cyanodiphenylcarbonimidate

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Refernces