(R)-2-(2-methylimidazo[2,1-b]thiazol-6-yl)-1-(2-(5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl)ethanone

Base Information

• Chemical Name: (R)-2-(2-methylimidazo[2,1-b]thiazol-6-yl)-1-(2-(5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl)ethanone
• CAS No.: 1334782-79-4
• Molecular Formula: C₂₉H₃₂N₆OS
• Molecular Weight: 512.679

Synonyms:

Chemical Property of (R)-2-(2-methylimidazo[2,1-b]thiazol-6-yl)-1-(2-(5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl)ethanone

Chemical Property:

Purity/Quality:

99%, ^*data from raw suppliers

PF5190457 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: PF 5190457 is a potent, selective, and orally bioavailable ghrelin receptor inverse agonist.

Technology Process of (R)-2-(2-methylimidazo[2,1-b]thiazol-6-yl)-1-(2-(5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl)ethanone

There total 24 articles about (R)-2-(2-methylimidazo[2,1-b]thiazol-6-yl)-1-(2-(5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl)ethanone 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: 79.0%

(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)acetic acid hydrochloride (1334784-86-9) + 2-[(1R)-5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane dihydrochloride → (R)-2-(2-methylimidazo[2,1-b]thiazol-6-yl)-1-(2-(5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl)ethanone (1334782-79-4)

Guidance literature:

(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)acetic acid hydrochloride; With triethylamine; 1,1'-carbonyldiimidazole; In dichloromethane; at 40 ℃; for 2h;

2-[(1R)-5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane dihydrochloride; In dichloromethane; at 40 ℃; for 2h; Product distribution / selectivity;

Reference yield: 63.0%

(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)acetic acid hydrochloride (1334784-86-9) + C21H26N4*ClH → (R)-2-(2-methylimidazo[2,1-b]thiazol-6-yl)-1-(2-(5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl)ethanone (1334782-79-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/acs.jmedchem.8b00794

Reference yield:

5-Bromo-1-indanone (34598-49-7) → (R)-2-(2-methylimidazo[2,1-b]thiazol-6-yl)-1-(2-(5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl)ethanone (1334782-79-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 4 h / -10 - 0 °C / Inert atmosphere

2.1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / 3 - 15 °C / Inert atmosphere

3.1: tin(II) chloride dihdyrate / methanol / 20 °C

3.2: 1 h

4.1: methanol / 16 h / 50 °C

4.2: 26 h / 20 - 60 °C / Inert atmosphere

5.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 110 °C / Inert atmosphere

6.1: sodium hydroxide / bis-triphenylphosphine-palladium(II) chloride / toluene / 5 h / 90 °C / Inert atmosphere

7.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C

8.1: triethylamine; 1,1'-carbonyldiimidazole / dichloromethane / 2 h / 40 °C

8.2: 2 h / 40 °C

With hydrogenchloride; tin(II) chloride dihdyrate; dimethylsulfide borane complex; diphenyl phosphoryl azide; potassium acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1'-carbonyldiimidazole; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; bis-triphenylphosphine-palladium(II) chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene;

upstream raw materials:

5-Bromo-1-indanone

1-tert-Butyl 4-methyl piperidine-1,4-dicarboxylate

4-methyl-6-chloropyrimidine

2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester

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