1,2-DIHYDRO-2-[(2-METHYL-4-PYRIDINYL)METHYL]-1-OXO-8-(2-PYRIMIDINYLMETHOXY)-4-(3,4,5-TRIMETHOXYPHENYL)-2,7-NAPHTHYRIDINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE

Base Information

• Chemical Name: 1,2-DIHYDRO-2-[(2-METHYL-4-PYRIDINYL)METHYL]-1-OXO-8-(2-PYRIMIDINYLMETHOXY)-4-(3,4,5-TRIMETHOXYPHENYL)-2,7-NAPHTHYRIDINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE
• CAS No.: 324572-92-1
• Molecular Formula: C₃₁H₂₉N₅O₇
• Molecular Weight: 583.601
• Mol file: 324572-92-1.mol

Synonyms:1,2-DIHYDRO-2-[(2-METHYL-4-PYRIDINYL)METHYL]-1-OXO-8-(2-PYRIMIDINYLMETHOXY)-4-(3,4,5-TRIMETHOXYPHENYL)-2,7-NAPHTHYRIDINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE;2-(2-METHYLPYRIDIN-4-YL)METHYL-4-(3,4,5-TRIMETHOXYPHENYL)-8-(PYRIMIDIN-2-YL)METHOXY-1,2-DIHYDRO-1-OXO-2,7-NAPHTHYRIDINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE;T-0156;T 0156 HYDROCHLORIDE;1,2-Dihydro-2-((2-methyl-4-pyridinyl)methyl)-1-oxo-8-(2-pyrimidinylmethoxy)-4-(3,4,5-trimethoxyphenyl)-2,7-naphthyridine;T0156HCl;2-(2-Methylpyridin-4-yl)methyl-4-(3,4,5-trimethoxyphenyl)-8-(pyrimidin-2-yl)methoxy-1,2-dihydro-1-oxo-2,7-naphthyridine-3-carboxylic acid methyl ester hydrochloride;1,2-DIHYDRO-2-[(2-METHYL-4-PYRIDINYL)METHYL]-1-OXO-8-(2-PYRIMIDINYLMETHOXY)-4-(3,4,5-TRIMETHOXYPHENYL)-2,7-NAPHTHYRIDINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE

Chemical Property of 1,2-DIHYDRO-2-[(2-METHYL-4-PYRIDINYL)METHYL]-1-OXO-8-(2-PYRIMIDINYLMETHOXY)-4-(3,4,5-TRIMETHOXYPHENYL)-2,7-NAPHTHYRIDINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE

Chemical Property:

• Vapor Pressure: 3.22E-24mmHg at 25°C
• Boiling Point: 779.1°C at 760 mmHg
• PKA: 5.53±0.10(Predicted)
• Flash Point: 425°C
• PSA: 136.78000
• Density: 1.329±0.06 g/cm3(Predicted)
• LogP: 4.79860
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble

Purity/Quality:

98%Min ^*data from raw suppliers

T0156hydrochloride ≥99%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Uses: T 0156 Hydrochloride is a potent and selective phosphodiesterase type 5 inhibitor.

Technology Process of 1,2-DIHYDRO-2-[(2-METHYL-4-PYRIDINYL)METHYL]-1-OXO-8-(2-PYRIMIDINYLMETHOXY)-4-(3,4,5-TRIMETHOXYPHENYL)-2,7-NAPHTHYRIDINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE

There total 11 articles about 1,2-DIHYDRO-2-[(2-METHYL-4-PYRIDINYL)METHYL]-1-OXO-8-(2-PYRIMIDINYLMETHOXY)-4-(3,4,5-TRIMETHOXYPHENYL)-2,7-NAPHTHYRIDINE-3-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE 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:

3,4,5-trimethoxy-benzaldehyde (86-81-7) → 2-((2-methylpyridin-4-yl)methyl)-4-(3,4,5-trimethoxyphenyl)-8-((pyrimidin-2-yl)methoxy)-1,2-dihydro-1-oxo-2,7-naphthyridine-3-carboxylic acid methyl ester (324572-92-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-BuLi; TMEDA / tetrahydrofuran

2.1: AcOH / dioxane

3.1: 94 percent / KMnO₄; aq. KOH / pyridine

4.1: KHCO₃ / dimethylformamide

5.1: DBU / toluene

5.2: AcOH / Heating

6.1: 98 percent / aq. NaOH / methanol

7.1: tetrahydrofuran

7.2: DEAD; PPh₃ / CH₂Cl₂

8.1: 79 percent / POCl₃ / dimethylformamide; CHCl₃

9.1: NaH

With potassium hydroxide; sodium hydroxide; potassium permanganate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium hydride; potassium hydrogencarbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0960-894X(03)00440-2

Reference yield:

3-Diisopropylaminocarbonyl-2-methoxypyridine (125335-74-2) → 2-((2-methylpyridin-4-yl)methyl)-4-(3,4,5-trimethoxyphenyl)-8-((pyrimidin-2-yl)methoxy)-1,2-dihydro-1-oxo-2,7-naphthyridine-3-carboxylic acid methyl ester (324572-92-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-BuLi; TMEDA / tetrahydrofuran

2.1: AcOH / dioxane

3.1: 94 percent / KMnO₄; aq. KOH / pyridine

4.1: KHCO₃ / dimethylformamide

5.1: DBU / toluene

5.2: AcOH / Heating

6.1: 98 percent / aq. NaOH / methanol

7.1: tetrahydrofuran

7.2: DEAD; PPh₃ / CH₂Cl₂

8.1: 79 percent / POCl₃ / dimethylformamide; CHCl₃

9.1: NaH

With potassium hydroxide; sodium hydroxide; potassium permanganate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium hydride; potassium hydrogencarbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0960-894X(03)00440-2

Reference yield:

4-methoxy-1-(3,4,5-trimethoxy-phenyl)-1H-furo[3,4-c]pyridin-3-one (324573-56-0) → 2-((2-methylpyridin-4-yl)methyl)-4-(3,4,5-trimethoxyphenyl)-8-((pyrimidin-2-yl)methoxy)-1,2-dihydro-1-oxo-2,7-naphthyridine-3-carboxylic acid methyl ester (324572-92-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 94 percent / KMnO₄; aq. KOH / pyridine

2.1: KHCO₃ / dimethylformamide

3.1: DBU / toluene

3.2: AcOH / Heating

4.1: 98 percent / aq. NaOH / methanol

5.1: tetrahydrofuran

5.2: DEAD; PPh₃ / CH₂Cl₂

6.1: 79 percent / POCl₃ / dimethylformamide; CHCl₃

7.1: NaH

With potassium hydroxide; sodium hydroxide; potassium permanganate; sodium hydride; potassium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trichlorophosphate; In tetrahydrofuran; pyridine; methanol; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0960-894X(03)00440-2

upstream raw materials:

2-pyrimidinemethanol

8-chloro-2-(2-methyl-pyridin-4-ylmethyl)-1-oxo-4-(3,4,5-trimethoxy-phenyl)-1,2-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

1-(2-methylpyridin-4-yl)methanamine

3,4,5-trimethoxy-benzaldehyde

Refernces