(2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]-5-(dimethylamino)-5-oxopentanoic acid

Base Information

• Chemical Name: (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]-5-(dimethylamino)-5-oxopentanoic acid
• CAS No.: 71074-44-7
• Molecular Formula: C22H27 N9 O4
• Molecular Weight: 481.51
• Mol file: 71074-44-7.mol

Synonyms:methotrexate-gamma-dimethylamide;MXT-gamma-DMA

Chemical Property of (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]-5-(dimethylamino)-5-oxopentanoic acid

Chemical Property:

• PKA: 3.55±0.10(Predicted)
• PSA: 193.55000
• Density: 1.422g/cm³
• LogP: 1.82530
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 9
• Exact Mass: 481.21860038
• Heavy Atom Count: 35
• Complexity: 746

Purity/Quality:

99%min ^*data from raw suppliers

MethotrexateDimethylamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C(=O)CCC(C(=O)O)NC(=O)C1=CC=C(C=C1)N(C)CC2=CN=C3C(=N2)C(=NC(=N3)N)N
• Isomeric SMILES: CN(C)C(=O)CC[C@@H](C(=O)O)NC(=O)C1=CC=C(C=C1)N(C)CC2=CN=C3C(=N2)C(=NC(=N3)N)N
• Uses: Methotrexate Dimethylamide is an impurity of Methotrexate (M260675) which is a folic acid antagonist. Used as a antineoplastic and antirheumatic.

Technology Process of (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]-5-(dimethylamino)-5-oxopentanoic acid

There total 8 articles about (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]-5-(dimethylamino)-5-oxopentanoic 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:

N-methyl-p-aminobenzoic acid (10541-83-0,937737-33-2) → (S)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-dimethylcarbamoyl-butyric acid (71074-44-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / 2 N NaOH / dioxane; H₂O / 0.5 h / 0 - 5 °C

2: 99 percent / SOCl₂ / benzene / 2 h / Heating

3: 89 percent / (i-Pr)2NEt / dioxane; H₂O

4: Et₃N / dimethylformamide; dioxane / 1 h / -10 °C

5: Et₃N / dimethylformamide; dioxane / 2 h / 25 °C

6: H₂ / 5percent Pd/C / dioxane / 20 h / Ambient temperature

7: N,N-dimethyl-acetamide / 120 h / 25 °C

With sodium hydroxide; thionyl chloride; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00344a018

Reference yield:

1-benzyl L-glutamate (13030-09-6) → (S)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-dimethylcarbamoyl-butyric acid (71074-44-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / (i-Pr)2NEt / dioxane; H₂O

2: Et₃N / dimethylformamide; dioxane / 1 h / -10 °C

3: Et₃N / dimethylformamide; dioxane / 2 h / 25 °C

4: H₂ / 5percent Pd/C / dioxane / 20 h / Ambient temperature

5: N,N-dimethyl-acetamide / 120 h / 25 °C

With hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00344a018

Reference yield:

4-<<(benzyloxy)carbonyl>methylamino>benzoic acid (2528-30-5) → (S)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-dimethylcarbamoyl-butyric acid (71074-44-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / SOCl₂ / benzene / 2 h / Heating

2: 89 percent / (i-Pr)2NEt / dioxane; H₂O

3: Et₃N / dimethylformamide; dioxane / 1 h / -10 °C

4: Et₃N / dimethylformamide; dioxane / 2 h / 25 °C

5: H₂ / 5percent Pd/C / dioxane / 20 h / Ambient temperature

6: N,N-dimethyl-acetamide / 120 h / 25 °C

With thionyl chloride; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00344a018

upstream raw materials:

6-bromomethyl-2,4-diaminopteridine hydrobromide

N-methyl-p-aminobenzoic acid

1-benzyl L-glutamate

4-<<(benzyloxy)carbonyl>methylamino>benzoic acid

Refernces