(2R,3R)-2-((3-carbamoyl-6-phenylpyrrolo[1,2-b] pyridazin-4-yl)amino)-3-hydroxybutyl dihydrogen phosphate

Base Information

• Chemical Name: (2R,3R)-2-((3-carbamoyl-6-phenylpyrrolo[1,2-b] pyridazin-4-yl)amino)-3-hydroxybutyl dihydrogen phosphate
• CAS No.: 1400878-19-4
• Molecular Formula: C₁₈H₂₁N₄O₆P
• Molecular Weight: 420.362
• Mol file: 1400878-19-4.mol

Synonyms:(2R,3R)-2-((3-carbamoyl-6-phenylpyrrolo[1,2-b] pyridazin-4-yl)amino)-3-hydroxybutyl dihydrogen phosphate

Chemical Property of (2R,3R)-2-((3-carbamoyl-6-phenylpyrrolo[1,2-b] pyridazin-4-yl)amino)-3-hydroxybutyl dihydrogen phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-((3-carbamoyl-6-phenylpyrrolo[1,2-b] pyridazin-4-yl)amino)-3-hydroxybutyl dihydrogen phosphate

There total 8 articles about (2R,3R)-2-((3-carbamoyl-6-phenylpyrrolo[1,2-b] pyridazin-4-yl)amino)-3-hydroxybutyl dihydrogen phosphate 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: 74.9%

dibenzyl ((2R,3R)-3-(benzyloxy)-2-((3-carbamoyl-6-phenylpyrrolo[1,2-b] pyridazin-4-yl)amino)butyl)phosphate (1400878-18-3) → (2R,3R)-2-((3-carbamoyl-6-phenylpyrrolo[1,2-b] pyridazin-4-yl)amino)-3-hydroxybutyl dihydrogen phosphate (1400878-19-4)

Guidance literature:

With hydrogen; palladium(II) hydroxide; In ethanol; at 20 ℃; for 48h;

Reference yield:

methyl 1-amino-4-bromo-1H-pyrrole-2-carboxylate methanesulfonic acid salt (1400580-12-2) → (2R,3R)-2-((3-carbamoyl-6-phenylpyrrolo[1,2-b] pyridazin-4-yl)amino)-3-hydroxybutyl dihydrogen phosphate (1400878-19-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: isopropyl alcohol / 3 h / 85 °C / Inert atmosphere

1.2: 5 h / 85 °C / Inert atmosphere

2.1: trichlorophosphate / 3 h / 75 °C / Inert atmosphere

3.1: sulfuric acid / 2 h / 55 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 100 °C / Inert atmosphere

5.1: palladium diacetate; potassium phosphate; XPhos / 1,4-dioxane / 1 h / 100 °C / Inert atmosphere

6.1: 1H-tetrazole / tetrahydrofuran; dichloromethane / 1.5 h / 0 °C / Inert atmosphere

6.2: 0.5 h / Inert atmosphere

7.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 48 h / 20 °C

With 1H-tetrazole; potassium phosphate; sulfuric acid; 10 wt% Pd(OH)2 on carbon; hydrogen; palladium diacetate; N-ethyl-N,N-diisopropylamine; XPhos; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl acetamide; isopropyl alcohol; 5.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/acsmedchemlett.8b00508

Reference yield:

methyl 4-bromo-1H-pyrrole-2-carboxylate (934-05-4) → (2R,3R)-2-((3-carbamoyl-6-phenylpyrrolo[1,2-b] pyridazin-4-yl)amino)-3-hydroxybutyl dihydrogen phosphate (1400878-19-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

1.2: 0.5 h / 20 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: isopropyl alcohol / 3 h / 85 °C / Inert atmosphere

2.2: 5 h / 85 °C / Inert atmosphere

3.1: trichlorophosphate / 3 h / 75 °C / Inert atmosphere

4.1: sulfuric acid / 2 h / 55 °C / Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 100 °C / Inert atmosphere

6.1: palladium diacetate; potassium phosphate; XPhos / 1,4-dioxane / 1 h / 100 °C / Inert atmosphere

7.1: 1H-tetrazole / tetrahydrofuran; dichloromethane / 1.5 h / 0 °C / Inert atmosphere

7.2: 0.5 h / Inert atmosphere

8.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 48 h / 20 °C

With 1H-tetrazole; potassium phosphate; sulfuric acid; 10 wt% Pd(OH)2 on carbon; hydrogen; palladium diacetate; sodium hydride; N-ethyl-N,N-diisopropylamine; XPhos; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; isopropyl alcohol; mineral oil; 6.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/acsmedchemlett.8b00508

upstream raw materials:

dibenzyl ((2R,3R)-3-(benzyloxy)-2-((3-carbamoyl-6-phenylpyrrolo[1,2-b] pyridazin-4-yl)amino)butyl)phosphate

methyl 1-amino-4-bromo-1H-pyrrole-2-carboxylate methanesulfonic acid salt

methyl 4-bromo-1H-pyrrole-2-carboxylate

6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carbonitrile