4-[N-(2,4-DIAMINO-6-PTERIDINYLMETHYL)-N-METHYLAMINO] BENZOIC ACID

Base Information

• Chemical Name: 4-[N-(2,4-DIAMINO-6-PTERIDINYLMETHYL)-N-METHYLAMINO] BENZOIC ACID
• CAS No.: 19741-14-1
• Molecular Formula: C15H15N7O2
• Molecular Weight: 325.33
• Hs Code.: 2933990090
• Mol file: 19741-14-1.mol

Synonyms:Benzoicacid, p-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]- (6CI,8CI);2,4-Diamino-N10-methylpteroic acid;4-Amino-4-deoxy-10-methylpteroic acid;4-Amino-4-deoxy-N10-methylpteroic acid;4-Deoxy-4-amino-N10-methylpteroic acid;4-[N-[(2,4-Diaminopyrimido[4,5-b]pyrazin-6-yl)methyl]-N-methylamino]benzoic acid;NSC 131463;NSC 133723;

Chemical Property of 4-[N-(2,4-DIAMINO-6-PTERIDINYLMETHYL)-N-METHYLAMINO] BENZOIC ACID

Chemical Property:

• Vapor Pressure: 5.96E-20mmHg at 25°C
• Melting Point: 255 °C (dec.)(lit.)
• Refractive Index: 1.799
• Boiling Point: 689.3 °C at 760 mmHg
• PKA: 4.63±0.10(Predicted)
• Flash Point: 370.7 °C
• PSA: 144.14000
• Density: 1.532 g/cm³
• LogP: 2.08120
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: Aqueous Base, DMSO

Purity/Quality:

99%+ ^*data from raw suppliers

DAMPA ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43-52/53
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Uses: DAMPA is a Methotrexate (M260675) analog (1). DAMPA is an antitumor agent (2). DAMPA is a Methotrexate (M260675) analog

Technology Process of 4-[N-(2,4-DIAMINO-6-PTERIDINYLMETHYL)-N-METHYLAMINO] BENZOIC ACID

There total 16 articles about 4-[N-(2,4-DIAMINO-6-PTERIDINYLMETHYL)-N-METHYLAMINO] BENZOIC 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: 99.0%

methotrexate sodium salt (7532-09-4) → 4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid (19741-14-1)

Guidance literature:

With sodium acetate; zinc(II) chloride; at 37 ℃;

DOI:10.1021/jm00350a015

Reference yield: 91.0%

N,N-dimethyl acetamide (127-19-5,116057-81-9) + 2,4-diamino-6-(hydroxymethyl)pteridine (945-24-4) + 4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → 4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid (19741-14-1)

Guidance literature:

2,4-diamino-6-(hydroxymethyl)pteridine; With dibromotriphenylphosphorane; In N,N-dimethyl acetamide; at 20 ℃; for 24h; Inert atmosphere;

N,N-dimethyl acetamide; 4-amino-benzoic acid; for 72h;

Reference yield: 90.0%

N-methyl-p-aminobenzoic acid (10541-83-0,937737-33-2) + 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride (73978-41-3) → 4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid (19741-14-1)

Guidance literature:

2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride; In water; at 20 - 80 ℃; for 0.0833333h;

With dibromotriphenylphosphorane; In N,N-dimethyl acetamide; at 20 ℃; for 20h;

N-methyl-p-aminobenzoic acid; With N-ethyl-N,N-diisopropylamine; at 20 ℃; for 72h;

DOI:10.1016/j.ejmech.2018.07.045

upstream raw materials:

2,4,5,6-tetraaminopyrimidine

1,1,3-tribromoacetone

N-methyl-p-aminobenzoic acid

2,4-diamino-6-(hydroxymethyl)pteridine

Downstream raw materials:

4-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoyl}-morpholine

4-{[N-[(2,4-diamino-6-pteridinyl)methyl]-N-methyl]amino}benzoyl azide

2-{4-tert-butoxycarbonyl-2-[4-tert-butoxycarbonyl-2-(4-tert-butoxycarbonyl-4-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-butyrylamino)-butyrylamino]-butyrylamino}-pentanedioic acid 5-tert-butyl ester

α-tert-butyl γ-methyl N'-<4--N-methylamino>benzoyl>-L-glutamate

Refernces

• 1、 Oe,Kohashi,Iwai. "Uptake and metabolism of methotrexate by Crithidia fasciculata". . p. 1847 - 1852. Retrieved 1983.
• 2、 Peiró Cadahía, Jorge,Bondebjerg, Jon,Hansen, Christian A.,Previtali, Viola,Hansen, Anders E.,Andresen, Thomas L.,Clausen, Mads H.. "Synthesis and Evaluation of Hydrogen Peroxide Sensitive Prodrugs of Methotrexate and Aminopterin for the Treatment of Rheumatoid Arthritis". . p. 3503 - 3515. Retrieved 2018/05/01.