3A-benzyl-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-3(3aH)-one

Base Information

• Chemical Name: 3A-benzyl-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-3(3aH)-one
• CAS No.: 193274-04-3
• Molecular Formula: C14H17N3O
• Molecular Weight: 243.308
• DSSTox Substance ID: DTXSID001132517
• Mol file: 193274-04-3.mol

Synonyms:3A-benzyl-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-3(3aH)-one;193274-04-3;3a-benzyl-2-methyl-4,5,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one;SCHEMBL5295413;SRIVSGVZUKSXSC-UHFFFAOYSA-N;DTXSID001132517;F50938;3a-Benzyl-2-methyl-2,3a,4,5,6,7-hexahydro-pyrazolo[4,3-c]pyridin-3-one;2,3a,4,5,6,7-Hexahydro-2-methyl-3a-(phenylmethyl)-3H-pyrazolo[4,3-c]pyridin-3-one

Chemical Property of 3A-benzyl-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-3(3aH)-one

Chemical Property:

• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 243.137162174
• Heavy Atom Count: 18
• Complexity: 373

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1C(=O)C2(CNCCC2=N1)CC3=CC=CC=C3

Technology Process of 3A-benzyl-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-3(3aH)-one

There total 7 articles about 3A-benzyl-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-3(3aH)-one 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: 80.0%

2,3a,4,5,6,7-hexahydro-2-methyl-3-oxo-3a-(phenylmethyl)-5H-pyrazolo[4,3-c]pyridine-5-carboxylic acid 1,1-dimethylethyl ester (193274-02-1) → 3a-(R)-Benzyl-2-methyl-2,3a,4,5,6,7-hexahydro-pyrazolo[4,3-c]pyridin-3-one (193274-04-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 2.5h;

DOI:10.1016/S0968-0896(02)00433-9

Reference yield:

1-tert-butyl 3-ethyl 3-benzyl-4-oxopiperidine-1,3-dicarboxylate (219324-21-7) + methylhydrazine (60-34-4) → 3a-(R)-Benzyl-2-methyl-2,3a,4,5,6,7-hexahydro-pyrazolo[4,3-c]pyridin-3-one (193274-04-3)

Guidance literature:

With acetic acid; In toluene;

Reference yield:

methyl 4-oxonipecotate (108554-34-3,56026-52-9) → 3a-(R)-Benzyl-2-methyl-2,3a,4,5,6,7-hexahydro-pyrazolo[4,3-c]pyridin-3-one (193274-04-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 99 percent / 4,4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

2.1: NaH / dimethylformamide / 0.25 h / 20 °C

2.2: 89 percent / dimethylformamide / 42 h / 20 °C

3.1: ethanol / 8 h / Heating

3.2: 66 percent / toluene / 17 h / Heating

4.1: 80 percent / trifluoroacetic acid / CH₂Cl₂ / 2.5 h / 0 °C

With dmap; sodium hydride; trifluoroacetic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(02)00433-9

upstream raw materials:

2,3a,4,5,6,7-hexahydro-2-methyl-3-oxo-3a-(phenylmethyl)-5H-pyrazolo[4,3-c]pyridine-5-carboxylic acid 1,1-dimethylethyl ester

methyl 4-oxonipecotate

methyl 1-tert-butoxycarbonyl-4-oxo-3-piperidinecarboxylate

3-(R,S)-Benzyl-4-oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester

Downstream raw materials:

capromorelin

{1-[2-(3a-(R)-benzyl-2-methyl-3-oxo-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]pyridin-5-yl)-1-(R)-benzyloxymethyl-2-oxo-ethylcarbamoyl]-1-methyl-ethyl}carbamic acid tert-butyl ester

{1-[2-(3a-(S)-benzyl-2-methyl-3-oxo-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]pyridin-5-yl)-1-(R)-benzyloxymethyl-2-oxo-ethylcarbamoyl]-1-methyl-ethyl}carbamic acid tert-butyl ester

(R)-3a-benzyl-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-3(3aH)-one (2R,3R)-2,3-dihydroxysuccinate