N-[(4,4-difluorocyclohexyl)methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

Base Information

• Chemical Name: N-[(4,4-difluorocyclohexyl)methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide
• CAS No.: 1384875-15-3
• Molecular Formula: C₁₉H₂₆F₂N₆O₂S
• Molecular Weight: 440.517

Synonyms:N-[(4,4-difluorocyclohexyl)methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

Chemical Property of N-[(4,4-difluorocyclohexyl)methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of N-[(4,4-difluorocyclohexyl)methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

There total 6 articles about N-[(4,4-difluorocyclohexyl)methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide 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:

4-(bromomethyl)-1,1-difluorocyclohexane (858121-94-5) + ethyl bromide (74-96-4) + 4-(4-sulfamoyl-4,7-diazaspiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester (1384875-65-3) → N-[(4,4-difluorocyclohexyl)methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide (1384875-15-3) + N-[(4,4-difluorocyclohexyl)methyl]-N-ethyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide (1384875-16-4) + N,N-bis[(4,4-difluorocyclohexyl)methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide (1384875-17-5)

Guidance literature:

4-(bromomethyl)-1,1-difluorocyclohexane; 4-(4-sulfamoyl-4,7-diazaspiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester; With caesium carbonate; In N,N-dimethyl-formamide; at 45 ℃; for 16h;

ethyl bromide; With caesium carbonate; In N,N-dimethyl-formamide; at 45 ℃; for 2h;

With 2,2,2-trifluoroethanol; In N,N-dimethyl-formamide; at 100 ℃; for 1h;

Reference yield:

4-chloro-1H-pyrrolo[2,3-d]pyrimidine (3680-69-1) → N-[(4,4-difluorocyclohexyl)methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide (1384875-15-3) + N-[(4,4-difluorocyclohexyl)methyl]-N-ethyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide (1384875-16-4) + N,N-bis[(4,4-difluorocyclohexyl)methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide (1384875-17-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / water / 16 h / 100 °C

2.1: ammonium formate / palladium 10% on activated carbon / methanol / 0.5 h / Reflux

2.2: 0.25 h

3.1: SULFAMIDE / 1,4-dioxane / 6 h / Reflux

4.1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 0 - 20 °C

5.1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 45 °C

5.2: 2 h / 45 °C

5.3: 1 h / 100 °C

With ammonium formate; potassium carbonate; SULFAMIDE; caesium carbonate; palladium 10% on activated carbon; In 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;

Reference yield:

4-(4-benzyl-4,7-diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine (1261358-78-4) → N-[(4,4-difluorocyclohexyl)methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide (1384875-15-3) + N-[(4,4-difluorocyclohexyl)methyl]-N-ethyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide (1384875-16-4) + N,N-bis[(4,4-difluorocyclohexyl)methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide (1384875-17-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ammonium formate / palladium 10% on activated carbon / methanol / 0.5 h / Reflux

1.2: 0.25 h

2.1: SULFAMIDE / 1,4-dioxane / 6 h / Reflux

3.1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 0 - 20 °C

4.1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 45 °C

4.2: 2 h / 45 °C

4.3: 1 h / 100 °C

With ammonium formate; SULFAMIDE; caesium carbonate; palladium 10% on activated carbon; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

upstream raw materials:

4-(bromomethyl)-1,1-difluorocyclohexane

ethyl bromide

4-(4-sulfamoyl-4,7-diazaspiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

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