Pentafluorophenyl 4-{N-[(6R)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(propyl-2-ynyl)amino}benzoate

Base Information

• Chemical Name: Pentafluorophenyl 4-{N-[(6R)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(propyl-2-ynyl)amino}benzoate
• CAS No.: 157701-73-0
• Molecular Formula: C₂₈H₁₈F₅N₃O₃
• Molecular Weight: 539.461
• Mol file: 157701-73-0.mol

Synonyms:Pentafluorophenyl 4-{N-[(6R)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(propyl-2-ynyl)amino}benzoate

Chemical Property of Pentafluorophenyl 4-{N-[(6R)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(propyl-2-ynyl)amino}benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Pentafluorophenyl 4-{N-[(6R)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(propyl-2-ynyl)amino}benzoate

There total 14 articles about Pentafluorophenyl 4-{N-[(6R)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(propyl-2-ynyl)amino}benzoate 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: 68.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + p-[N-((6R)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]benzoic acid → Pentafluorophenyl 4-{N-[(6R)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(propyl-2-ynyl)amino}benzoate (157701-73-0)

Guidance literature:

Reference yield:

indan-5-amine (24425-40-9) → Pentafluorophenyl 4-{N-[(6R)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(propyl-2-ynyl)amino}benzoate (157701-73-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 81 percent / pyridine / ethyl acetate / 17 h / 20 °C

2.1: 97 percent / Br₂ / acetic acid / 0.5 h / 20 °C

3.1: 86 percent / 1-methyl-pyrrolidin-2-one / 0.5 h / 125 °C

4.1: 83 percent / H₂O₂ / aq. ethanol / 1 h / 50 - 55 °C

5.1: t-BuOK / dimethylsulfoxide / 0.5 h / 20 °C

5.2: 51 percent / dimethylsulfoxide / 24 h

6.1: 37 percent / tert-butyl hydroperoxide; CrO₃; H₂O / CH₂Cl₂ / 22 h / 20 °C

7.1: TsOH*H₂O; 3 Angstroem molecular sieves / 1,2-dimethoxy-ethane / 4 h / Heating

8.1: NaBH₃CN; CH₃COOH / methanol; 1,2-dimethoxy-ethane / 17 h / 20 °C

9.1: 77 percent / CaCO₃ / N,N-dimethyl-acetamide / 21 h / 98 - 105 °C

10.1: 93 percent / NaOH; H₂O / methanol / 24 h / 20 °C

11.1: trisHCl; ZnCl₂; H₂O / carboxypeptidase G₂ / H₂O / 10 h / 37 °C / pH 7.3 / Enzymatic reaction

12.1: pyridine / N,N-dimethyl-acetamide / 5 h / 20 °C

With pyridine; chromium(VI) oxide; tert.-butylhydroperoxide; sodium hydroxide; 3 A molecular sieve; potassium tert-butylate; water; dihydrogen peroxide; bromine; tris hydrochloride; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; calcium carbonate; zinc(II) chloride; carboxypeptidase G₂; In 1-methyl-pyrrolidin-2-one; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl acetamide; water; acetic acid; dimethyl sulfoxide; ethyl acetate; 1.1: Acetylation / 2.1: Bromination / 3.1: Substitution / 4.1: Cyclization / 5.1: Metallation / 5.2: Alkylation / 6.1: Oxidation / 7.1: Condensation / 8.1: Reduction / 9.1: Alkylation / 10.1: Hydrolysis / 11.1: Hydrolysis / 12.1: Esterification;

Reference yield:

5-acetylamino-6-bromoindane (157701-33-2) → Pentafluorophenyl 4-{N-[(6R)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(propyl-2-ynyl)amino}benzoate (157701-73-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 86 percent / 1-methyl-pyrrolidin-2-one / 0.5 h / 125 °C

2.1: 83 percent / H₂O₂ / aq. ethanol / 1 h / 50 - 55 °C

3.1: t-BuOK / dimethylsulfoxide / 0.5 h / 20 °C

3.2: 51 percent / dimethylsulfoxide / 24 h

4.1: 37 percent / tert-butyl hydroperoxide; CrO₃; H₂O / CH₂Cl₂ / 22 h / 20 °C

5.1: TsOH*H₂O; 3 Angstroem molecular sieves / 1,2-dimethoxy-ethane / 4 h / Heating

6.1: NaBH₃CN; CH₃COOH / methanol; 1,2-dimethoxy-ethane / 17 h / 20 °C

7.1: 77 percent / CaCO₃ / N,N-dimethyl-acetamide / 21 h / 98 - 105 °C

8.1: 93 percent / NaOH; H₂O / methanol / 24 h / 20 °C

9.1: trisHCl; ZnCl₂; H₂O / carboxypeptidase G₂ / H₂O / 10 h / 37 °C / pH 7.3 / Enzymatic reaction

10.1: pyridine / N,N-dimethyl-acetamide / 5 h / 20 °C

With pyridine; chromium(VI) oxide; tert.-butylhydroperoxide; sodium hydroxide; 3 A molecular sieve; potassium tert-butylate; water; dihydrogen peroxide; tris hydrochloride; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; calcium carbonate; zinc(II) chloride; carboxypeptidase G₂; In 1-methyl-pyrrolidin-2-one; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; 1.1: Substitution / 2.1: Cyclization / 3.1: Metallation / 3.2: Alkylation / 4.1: Oxidation / 5.1: Condensation / 6.1: Reduction / 7.1: Alkylation / 8.1: Hydrolysis / 9.1: Hydrolysis / 10.1: Esterification;

upstream raw materials:

pentafluorophenyl trifloroacetate

4-{N-[(6R/6S)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoic acid

indan-5-amine

5-acetylamino-6-bromoindane

Downstream raw materials:

2-{4-[(2-methyl-4-oxo-4,6,7,8-tetrahydro-3H-cyclopenta[g]quinazolin-6-yl)-prop-2-ynyl-amino]-benzoylamino}-5-(1H-[1,2,4]triazole-3-sulfonyl)-pentanoic acid methyl ester

4-[3-tert-butoxycarbonyl-1-(1H-tetrazol-5-yl)-propylcarbamoyl]-2-{4-[(2-methyl-4-oxo-4,6,7,8-tetrahydro-3H-cyclopenta[g]quinazolin-6-yl)-prop-2-ynyl-amino]-benzoylamino}-butyric acid tert-butyl ester