1-methyl-8-{2-trifluoromethoxy-5-[(1-methyl-piperidine-4-carbonyl)-amino]-phenylamino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Base Information

• Chemical Name: 1-methyl-8-{2-trifluoromethoxy-5-[(1-methyl-piperidine-4-carbonyl)-amino]-phenylamino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide
• CAS No.: 1034616-60-8
• Molecular Formula: C₂₅H₂₇F₃N₈O₃
• Molecular Weight: 544.536
• Mol file: 1034616-60-8.mol

Synonyms:1-methyl-8-{2-trifluoromethoxy-5-[(1-methyl-piperidine-4-carbonyl)-amino]-phenylamino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Chemical Property of 1-methyl-8-{2-trifluoromethoxy-5-[(1-methyl-piperidine-4-carbonyl)-amino]-phenylamino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-methyl-8-{2-trifluoromethoxy-5-[(1-methyl-piperidine-4-carbonyl)-amino]-phenylamino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

There total 5 articles about 1-methyl-8-{2-trifluoromethoxy-5-[(1-methyl-piperidine-4-carbonyl)-amino]-phenylamino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-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:

1-methylpiperidine-4-carboxylic acid (68947-43-3) + 1-methyl-8-{[5-amino-2-(trifluoromethoxy)phenyl]amino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (1034616-54-0) → 1-methyl-8-{2-trifluoromethoxy-5-[(1-methyl-piperidine-4-carbonyl)-amino]-phenylamino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (1034616-60-8)

Guidance literature:

With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; at 20 ℃; for 4h;

DOI:10.1016/j.bmcl.2011.03.054

Reference yield:

5-nitro-2-(trifluoromethoxy)aniline (158579-82-9) → 1-methyl-8-{2-trifluoromethoxy-5-[(1-methyl-piperidine-4-carbonyl)-amino]-phenylamino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (1034616-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium diacetate; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / N,N-dimethyl-formamide / 80 °C

2: iron; ammonium chloride / methanol; water / Reflux

3: benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / 4 h / 20 °C

With palladium diacetate; iron; potassium carbonate; ammonium chloride; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; In methanol; water; N,N-dimethyl-formamide; 1: Buchwald-Hartwig reaction;

DOI:10.1016/j.bmcl.2011.03.054

Reference yield:

8-iodo-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (802537-20-8) → 1-methyl-8-{2-trifluoromethoxy-5-[(1-methyl-piperidine-4-carbonyl)-amino]-phenylamino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (1034616-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium diacetate; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / N,N-dimethyl-formamide / 80 °C

2: iron; ammonium chloride / methanol; water / Reflux

3: benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / 4 h / 20 °C

With palladium diacetate; iron; potassium carbonate; ammonium chloride; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; In methanol; water; N,N-dimethyl-formamide; 1: Buchwald-Hartwig reaction;

DOI:10.1016/j.bmcl.2011.03.054

upstream raw materials:

1-methylpiperidine-4-carboxylic acid

1-methyl-8-{[5-amino-2-(trifluoromethoxy)phenyl]amino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

8-iodo-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

5-nitro-2-(trifluoromethoxy)aniline