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

Base Information

• Chemical Name: N-(4-{N-[(6S)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoyl)-L-glutamic acid
• CAS No.: 157701-05-8
• Molecular Formula: C₂₇H₂₆N₄O₆
• Molecular Weight: 502.527
• Mol file: 157701-05-8.mol

Synonyms:N-(4-{N-[(6S)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoyl)-L-glutamic acid

Chemical Property of N-(4-{N-[(6S)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoyl)-L-glutamic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(4-{N-[(6S)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoyl)-L-glutamic acid

There total 13 articles about N-(4-{N-[(6S)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoyl)-L-glutamic acid 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%

N-(4-{N-[(6RS)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoyl)-L-glutamic acid (157701-04-7) → 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 (174487-71-9) + 4-{N-[(6S)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoic acid (157701-39-8) + N-(4-{N-[(6S)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoyl)-L-glutamic acid (157701-05-8)

Guidance literature:

With water; tris hydrochloride; zinc(II) chloride; carboxypeptidase G₂; In water; at 37 ℃; for 10h; pH=7.3; Enzymatic reaction;

Reference yield:

indan-5-amine (24425-40-9) → N-(4-{N-[(6S)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoyl)-L-glutamic acid (157701-05-8)

Guidance literature:

Multi-step reaction with 11 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: 80 percent / trisHCl; ZnCl₂; H₂O / carboxypeptidase G₂ / H₂O / 10 h / 37 °C / pH 7.3 / Enzymatic reaction

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;

Reference yield:

5-acetylamino-6-bromoindane (157701-33-2) → N-(4-{N-[(6S)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoyl)-L-glutamic acid (157701-05-8)

Guidance literature:

Multi-step reaction with 9 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: 80 percent / trisHCl; ZnCl₂; H₂O / carboxypeptidase G₂ / H₂O / 10 h / 37 °C / pH 7.3 / Enzymatic reaction

With 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;

upstream raw materials:

N-(4-{N-[(6RS)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoyl)-L-glutamic acid

indan-5-amine

5-acetylamino-6-bromoindane

5-acetamidoindane

Downstream raw materials:

4-{N-[(6S)-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-[(6S)-2,3-dimethyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoate

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