5-amino-3,4-dimethyl-N-(4-((trifluoromethyl)sulfonyl)benzyl)thieno-[2,3-c]pyridazine-6-carboxamide

Base Information

• Chemical Name: 5-amino-3,4-dimethyl-N-(4-((trifluoromethyl)sulfonyl)benzyl)thieno-[2,3-c]pyridazine-6-carboxamide
• CAS No.: 1451993-15-9
• Molecular Formula: C₁₇H₁₅F₃N₄O₃S₂
• Molecular Weight: 444.458
• Mol file: 1451993-15-9.mol

Synonyms:5-amino-3,4-dimethyl-N-(4-((trifluoromethyl)sulfonyl)benzyl)thieno-[2,3-c]pyridazine-6-carboxamide

Chemical Property of 5-amino-3,4-dimethyl-N-(4-((trifluoromethyl)sulfonyl)benzyl)thieno-[2,3-c]pyridazine-6-carboxamide

Chemical Property:

• Density: 1.514±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

VU0467154 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: VU0467154 is a positive allosteric modulator of the M4 muscarinic acetylcholine receptor that potentiates acetylcholine responses in CHO cells expressing M4 receptors (EC50s = 17.7, 630, and 1,000 nM for rat, human, and cynomolgus monkey receptors, respectively). It is selective for M4 over M1-3 and M5 receptors and a panel of receptors, transporters, and cation channels when used at a concentration of 10 μM. In vivo, VU0467154 (3-56.6 mg/kg, p.o.) reverses amphetamine-induced hyperlocomotion in rats. It reverses MK-801-induced hyperlocomotion, deficits in a pairwise visual discrimination task, and impairments in the acquisition of contextual fear conditioning in wild-type, but not M4 knockout, mice. VU0467154 (3-30 mg/kg) also increases freezing behavior in contextual and tone fear conditioning tests in wild-type mice when administered prior to the conditioning session. Chronic administration of VU0467154 (10 mg/kg once daily) reduces motor incoordination and prevents decreases in locomotion in the YAC128 transgenic mouse model of Huntington''s disease.
• Uses: VU 0467154, is a positive allosteric modulators of the M4 muscarinic acetylcholine receptor (mAChR), robustly potentiates the response to ACh with pEC50s of 7.75, 6.2 and 6 for rat, human and cynomolgus monkey (cyno) M4 receptor, respectively.

Technology Process of 5-amino-3,4-dimethyl-N-(4-((trifluoromethyl)sulfonyl)benzyl)thieno-[2,3-c]pyridazine-6-carboxamide

There total 4 articles about 5-amino-3,4-dimethyl-N-(4-((trifluoromethyl)sulfonyl)benzyl)thieno-[2,3-c]pyridazine-6-carboxamide 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:

(4-((trifluoromethyl)sulfonyl)phenyl)methanamine (771473-17-7) + 5-amino-3,4-dimethylthieno[2,3-c]pyridazine-6-carboxylic acid (1452226-14-0) → 5-amino-3,4-dimethyl-N-(4-((trifluoromethyl)sulfonyl)benzyl)thieno-[2,3-c]pyridazine-6-carboxamide (1451993-15-9)

Guidance literature:

5-amino-3,4-dimethylthieno[2,3-c]pyridazine-6-carboxylic acid; With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 0.75h;

(4-((trifluoromethyl)sulfonyl)phenyl)methanamine; In N,N-dimethyl-formamide; for 0.333333h;

Reference yield:

(4-((trifluoromethyl)sulfonyl)phenyl)methanamine (771473-17-7) + sodium 5-amino-3,4-dimethylthieno[2,3-c]pyridazine-6-carboxylate (1451998-17-6) → 5-amino-3,4-dimethyl-N-(4-((trifluoromethyl)sulfonyl)benzyl)thieno-[2,3-c]pyridazine-6-carboxamide (1451993-15-9)

Guidance literature:

sodium 5-amino-3,4-dimethylthieno[2,3-c]pyridazine-6-carboxylate; With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 0.75h;

(4-((trifluoromethyl)sulfonyl)phenyl)methanamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.333333h;

DOI:10.1021/cn500128b

Reference yield:

3-chloro-5,6-dimethylpyridazine-4-carbonitrile (93824-72-7) → 5-amino-3,4-dimethyl-N-(4-((trifluoromethyl)sulfonyl)benzyl)thieno-[2,3-c]pyridazine-6-carboxamide (1451993-15-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / methanol; water / 0.5 h / 150 °C / Microwave irradiation; Sealed tube

2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.75 h / 20 °C

2.2: 0.33 h / 20 °C

With N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/cn500128b

upstream raw materials:

4-[(trifluoromethyl)sulfonyl] benzonitrile

(4-((trifluoromethyl)sulfonyl)phenyl)methanamine

5-amino-3,4-dimethylthieno[2,3-c]pyridazine-6-carboxylic acid

3-chloro-5,6-dimethylpyridazine-4-carbonitrile

Refernces

• 1、 -. "SUBSTITUTED 5-AMINOTHIENO[2,3-C]PYRIDAZINE-6-CARBOXAMIDE ANALOGS AS POSITIVE ALLOSTERIC MODULATORS OF THE MUSCARINIC ACETYLCHOLINE RECEPTOR M4". . . Retrieved 2013/09/12.