(S)-6-((3,5-dimethyl-1H-pyrazol-4-yl)methyl)-5-(4-hydroxyisoxazolidine-2-carbonyl)-1-isobutyl-3-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: (S)-6-((3,5-dimethyl-1H-pyrazol-4-yl)methyl)-5-(4-hydroxyisoxazolidine-2-carbonyl)-1-isobutyl-3-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione
• CAS No.: 496791-37-8
• Molecular Formula: C21H27N5O5S
• Molecular Weight: 461.53500
• European Community (EC) Number: 838-913-9
• ChEMBL ID: CHEMBL375166
• DSSTox Substance ID: DTXSID70436993
• Nikkaji Number: J2.810.168F
• Wikidata: Q72443636
• Mol file: 496791-37-8.mol

Synonyms:AR C155858;AR-C155858

Chemical Property of (S)-6-((3,5-dimethyl-1H-pyrazol-4-yl)methyl)-5-(4-hydroxyisoxazolidine-2-carbonyl)-1-isobutyl-3-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Chemical Property:

• Melting Point: 198-202∶C
• Boiling Point: 763.1±70.0 °C(Predicted)
• PKA: 13.53±0.20(Predicted)
• PSA: 150.69000
• Density: 1.395
• LogP: 1.03460
• Solubility.: insoluble in H2O; ≥52.5 mg/mL in DMSO; ≥57.8 mg/mL in EtOH
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 461.17329015
• Heavy Atom Count: 32
• Complexity: 769

Purity/Quality:

97% ^*data from raw suppliers

AR-C155858 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=NN1)C)CC2=C(C3=C(S2)N(C(=O)N(C3=O)C)CC(C)C)C(=O)N4CC(CO4)O
• Isomeric SMILES: CC1=C(C(=NN1)C)CC2=C(C3=C(S2)N(C(=O)N(C3=O)C)CC(C)C)C(=O)N4C[C@@H](CO4)O
• Uses: AR-C155858 is a potent inhibitor of monocarboxylate transporters MCT1 and MCT2 that binds to an intracellular site involving transmembrane helices 7-10.

Technology Process of (S)-6-((3,5-dimethyl-1H-pyrazol-4-yl)methyl)-5-(4-hydroxyisoxazolidine-2-carbonyl)-1-isobutyl-3-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

There total 4 articles about (S)-6-((3,5-dimethyl-1H-pyrazol-4-yl)methyl)-5-(4-hydroxyisoxazolidine-2-carbonyl)-1-isobutyl-3-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione 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: 62.0%

(4S)-isoxazolidin-2-ium-4-ol chloride (338464-48-5) + 6-[(3,5-dimethyl-1H-pyrazol-4-yl)methyl]-1-isobutyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylic acid (496791-38-9) → AR-C155858 (496791-37-8)

Guidance literature:

6-[(3,5-dimethyl-1H-pyrazol-4-yl)methyl]-1-isobutyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylic acid; With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 18 - 25 ℃; for 0.5h;

(4S)-isoxazolidin-2-ium-4-ol chloride; In dichloromethane; at 18 - 25 ℃; for 3h;

DOI:10.1021/jm060995h

Reference yield:

methyl 6-bromomethyl-1-isobutyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate (491614-00-7) → AR-C155858 (496791-37-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: CHCl₃ / 0.25 h / Heating

1.2: aq. hydrazine / CH₂Cl₂ / 16 h / 18 - 25 °C

2.1: 1.85 g / aq. NaOH / tetrahydrofuran; methanol / 1 h / 18 - 25 °C

3.1: 1-hydroxybenzotriazole hydrate; 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide*HCl / CH₂Cl₂ / 0.5 h / 18 - 25 °C

3.2: 62 percent / CH₂Cl₂ / 3 h / 18 - 25 °C

With sodium hydroxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane; chloroform;

DOI:10.1021/jm060995h

Reference yield:

1-isobutyl-3,6-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-thieno[2,3-d]pyrimidine-5-carboxylic acid methyl ester → AR-C155858 (496791-37-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 76 percent / N-bromosuccinimide / CHCl₃ / Heating; irradiation

2.1: CHCl₃ / 0.25 h / Heating

2.2: aq. hydrazine / CH₂Cl₂ / 16 h / 18 - 25 °C

3.1: 1.85 g / aq. NaOH / tetrahydrofuran; methanol / 1 h / 18 - 25 °C

4.1: 1-hydroxybenzotriazole hydrate; 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide*HCl / CH₂Cl₂ / 0.5 h / 18 - 25 °C

4.2: 62 percent / CH₂Cl₂ / 3 h / 18 - 25 °C

With sodium hydroxide; N-Bromosuccinimide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane; chloroform;

DOI:10.1021/jm060995h

upstream raw materials:

(4S)-isoxazolidin-2-ium-4-ol chloride

6-[(3,5-dimethyl-1H-pyrazol-4-yl)methyl]-1-isobutyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylic acid

methyl 6-bromomethyl-1-isobutyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

methyl 6-[(3,5-dimethyl-1H-pyrazol-4-yl)methyl]-1-isobutyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

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