methyl N^α-{1-[(2,4-diaminopteridin-6-yl)methyl]indolin-5-ylcarbonyl}-N^δ-phenyl-L-glutaminate

Base Information

• Chemical Name: methyl N^α-{1-[(2,4-diaminopteridin-6-yl)methyl]indolin-5-ylcarbonyl}-N^δ-phenyl-L-glutaminate
• CAS No.: 142166-24-3
• Molecular Formula: C₂₈H₂₉N₉O₄
• Molecular Weight: 555.596

Synonyms:methyl N^α-{1-[(2,4-diaminopteridin-6-yl)methyl]indolin-5-ylcarbonyl}-N^δ-phenyl-L-glutaminate

Chemical Property of methyl N^α-{1-[(2,4-diaminopteridin-6-yl)methyl]indolin-5-ylcarbonyl}-N^δ-phenyl-L-glutaminate

Chemical Property:

Purity/Quality:

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Technology Process of methyl N^α-{1-[(2,4-diaminopteridin-6-yl)methyl]indolin-5-ylcarbonyl}-N^δ-phenyl-L-glutaminate

There total 8 articles about methyl N^α-{1-[(2,4-diaminopteridin-6-yl)methyl]indolin-5-ylcarbonyl}-N^δ-phenyl-L-glutaminate 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:

N-tert-butoxycarbonylglutamic acid methyl ester (72086-72-7) → methyl Nα-{1-[(2,4-diaminopteridin-6-yl)methyl]indolin-5-ylcarbonyl}-Nδ-phenyl-L-glutaminate (142166-24-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) / CH₂Cl₂ / Ambient temperature

2: 98 percent / TFA / 0.5 h / Ambient temperature

3: aq. K₂CO₃ / CH₂Cl₂ / 10 h / Ambient temperature

4: H₂ / 5percent Pd/C / methanol / Ambient temperature

5: N,N-dimethyl-acetamide / 6 h / 55 °C

With hydrogen; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl acetamide;

DOI:10.1248/cpb.45.1146

Reference yield:

aniline (62-53-3) → methyl Nα-{1-[(2,4-diaminopteridin-6-yl)methyl]indolin-5-ylcarbonyl}-Nδ-phenyl-L-glutaminate (142166-24-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) / CH₂Cl₂ / Ambient temperature

2: 98 percent / TFA / 0.5 h / Ambient temperature

3: aq. K₂CO₃ / CH₂Cl₂ / 10 h / Ambient temperature

4: H₂ / 5percent Pd/C / methanol / Ambient temperature

5: N,N-dimethyl-acetamide / 6 h / 55 °C

With hydrogen; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl acetamide;

DOI:10.1248/cpb.45.1146

Reference yield:

1-carbobenzoxy-5-carboxyindoline (142165-63-7) → methyl Nα-{1-[(2,4-diaminopteridin-6-yl)methyl]indolin-5-ylcarbonyl}-Nδ-phenyl-L-glutaminate (142166-24-3)

Guidance literature:

Multi-step reaction with 4 steps

1: SOCl₂ / dimethylformamide / 1 h

2: aq. K₂CO₃ / CH₂Cl₂ / 10 h / Ambient temperature

3: H₂ / 5percent Pd/C / methanol / Ambient temperature

4: N,N-dimethyl-acetamide / 6 h / 55 °C

With thionyl chloride; hydrogen; potassium carbonate; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide;

DOI:10.1248/cpb.45.1146

upstream raw materials:

6-bromomethyl-2,4-diaminopteridine hydrobromide

(S)-2-[(2,3-Dihydro-1H-indole-5-carbonyl)-amino]-4-phenylcarbamoyl-butyric acid methyl ester

N-tert-butoxycarbonylglutamic acid methyl ester

aniline

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