N-[4-[1-[(2,6-Difluorophenyl)methyl]-1,2,3,4-tetrahydro-5-[[methyl(phenylmethyl)amino]methyl]-2,4-dioxo-3-phenylthieno[2,3-d]pyrimidin-6-yl]phenyl]-N'-hydroxyurea

Base Information

• Chemical Name: N-[4-[1-[(2,6-Difluorophenyl)methyl]-1,2,3,4-tetrahydro-5-[[methyl(phenylmethyl)amino]methyl]-2,4-dioxo-3-phenylthieno[2,3-d]pyrimidin-6-yl]phenyl]-N'-hydroxyurea
• CAS No.: 308831-77-8
• Molecular Formula: C₃₅H₂₉F₂N₅O₄S
• Molecular Weight: 653.709
• DSSTox Substance ID: DTXSID201099559
• Pharos Ligand ID: V6KTVH16Y5XV
• ChEMBL ID: CHEMBL277214
• Mol file: 308831-77-8.mol

Synonyms:CHEMBL277214;SCHEMBL4253402;DTXSID201099559;BDBM50122671;1-{4-[5-[(Benzyl-methyl-amino)-methyl]-1-(2,6-difluoro-benzyl)-2,4-dioxo-3-phenyl-1,2,3,4-tetrahydro-thieno[2,3-d]pyrimidin-6-yl]-phenyl}-3-hydroxy-urea;HCL.H2O;308831-77-8;N-[4-[1-[(2,6-Difluorophenyl)methyl]-1,2,3,4-tetrahydro-5-[[methyl(phenylmethyl)amino]methyl]-2,4-dioxo-3-phenylthieno[2,3-d]pyrimidin-6-yl]phenyl]-N'-hydroxyurea

Chemical Property of N-[4-[1-[(2,6-Difluorophenyl)methyl]-1,2,3,4-tetrahydro-5-[[methyl(phenylmethyl)amino]methyl]-2,4-dioxo-3-phenylthieno[2,3-d]pyrimidin-6-yl]phenyl]-N'-hydroxyurea

Chemical Property:

• XLogP3: 5.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 653.19083192
• Heavy Atom Count: 47
• Complexity: 1080

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN(CC1=CC=CC=C1)CC2=C(SC3=C2C(=O)N(C(=O)N3CC4=C(C=CC=C4F)F)C5=CC=CC=C5)C6=CC=C(C=C6)NC(=O)NO

Technology Process of N-[4-[1-[(2,6-Difluorophenyl)methyl]-1,2,3,4-tetrahydro-5-[[methyl(phenylmethyl)amino]methyl]-2,4-dioxo-3-phenylthieno[2,3-d]pyrimidin-6-yl]phenyl]-N'-hydroxyurea

There total 11 articles about N-[4-[1-[(2,6-Difluorophenyl)methyl]-1,2,3,4-tetrahydro-5-[[methyl(phenylmethyl)amino]methyl]-2,4-dioxo-3-phenylthieno[2,3-d]pyrimidin-6-yl]phenyl]-N'-hydroxyurea 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: 100.0%

5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-[4-[3-(2,4-dimethoxybenzyloxy)ureido]phenyl]-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (481049-97-2) → 5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-[4-(3-hydroxyureido)phenyl]-3-phenylthieno[2,3-d]pyrimidine-2,4-(1H,3H)-dione (308831-77-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.333333h;

DOI:10.1021/jm020180i

Reference yield:

2,6-difluorobenzyl chloride (697-73-4) → 5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-[4-(3-hydroxyureido)phenyl]-3-phenylthieno[2,3-d]pyrimidine-2,4-(1H,3H)-dione (308831-77-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 90 percent / KI; K₂CO₃ / dimethylformamide / 4 h / 20 °C

2.1: NBS; AIBN / chlorobenzene / 1.5 h / 90 °C

3.1: 33.0 g / i-Pr₂NEt / dimethylformamide / 2 h / 20 °C

4.1: 87 percent / HCl; HCO₂H / 10 percent Pd/C/water / diethyl ether / 3.5 h / 20 °C / atmospheric pressure

5.1: Et₃N / CH₂Cl₂ / 20 °C

5.2: CH₂Cl₂ / 20 °C

6.1: 100 percent / TFA / CH₂Cl₂ / 0.33 h / 20 °C

With hydrogenchloride; N-Bromosuccinimide; formic acid; 2,2'-azobis(isobutyronitrile); potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; potassium iodide; 10 percent Pd/C/water; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; chlorobenzene;

DOI:10.1021/jm020180i

Reference yield:

1-(4-nitrophenyl)propan-2-one (5332-96-7) → 5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-[4-(3-hydroxyureido)phenyl]-3-phenylthieno[2,3-d]pyrimidine-2,4-(1H,3H)-dione (308831-77-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NH₄OAc; AcOH / toluene / 20 h / Heating

1.2: 67 percent / sulfur / ethanol / 2 h / 65 °C

2.1: pyridine / 2 h / 45 °C

3.1: 50.4 g / NaOMe / methanol / 6 h / 20 °C

4.1: 90 percent / KI; K₂CO₃ / dimethylformamide / 4 h / 20 °C

5.1: NBS; AIBN / chlorobenzene / 1.5 h / 90 °C

6.1: 33.0 g / i-Pr₂NEt / dimethylformamide / 2 h / 20 °C

7.1: 87 percent / HCl; HCO₂H / 10 percent Pd/C/water / diethyl ether / 3.5 h / 20 °C / atmospheric pressure

8.1: Et₃N / CH₂Cl₂ / 20 °C

8.2: CH₂Cl₂ / 20 °C

9.1: 100 percent / TFA / CH₂Cl₂ / 0.33 h / 20 °C

With pyridine; hydrogenchloride; N-Bromosuccinimide; formic acid; 2,2'-azobis(isobutyronitrile); ammonium acetate; sodium methylate; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; potassium iodide; 10 percent Pd/C/water; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; chlorobenzene; toluene;

DOI:10.1021/jm020180i

upstream raw materials:

5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-[4-[3-(2,4-dimethoxybenzyloxy)ureido]phenyl]-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

1-(4-nitrophenyl)propan-2-one

2,6-difluorobenzyl chloride

phenyl isocyanate