1-({(5S,7S)-3-[4-(ethyloxy)phenyl]-7-methyl-2-oxo-1-oxa-3-azaspiro[4.5]dec-7-yl}methyl)-1H-benzimidazole-6-carbonitril

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Chemical Name:1-({(5S,7S)-3-[4-(ethyloxy)phenyl]-7-methyl-2-oxo-1-oxa-3-azaspiro[4.5]dec-7-yl}methyl)-1H-benzimidazole-6-carbonitril
CAS No.:1416323-43-7
Molecular Formula:C₂₆H₂₈N₄O₃
Molecular Weight:444.533
Hs Code.:

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Chemical Property of 1-({(5S,7S)-3-[4-(ethyloxy)phenyl]-7-methyl-2-oxo-1-oxa-3-azaspiro[4.5]dec-7-yl}methyl)-1H-benzimidazole-6-carbonitril

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Technology Process of 1-({(5S,7S)-3-[4-(ethyloxy)phenyl]-7-methyl-2-oxo-1-oxa-3-azaspiro[4.5]dec-7-yl}methyl)-1H-benzimidazole-6-carbonitril

There total 14 articles about 1-({(5S,7S)-3-[4-(ethyloxy)phenyl]-7-methyl-2-oxo-1-oxa-3-azaspiro[4.5]dec-7-yl}methyl)-1H-benzimidazole-6-carbonitril 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: 3.7%

: 1-{[(1S,3S)-3-({[4-(ethyloxy)phenyl]amino}methyl)-3-hydroxy-1-methylcyclohexyl]methyl}-1H-benzimidazole-6-carbonitrile

: 530-62-1
1,1'-carbonyldiimidazole

: 1416323-43-7
1-({(5S,7S)-3-[4-(ethyloxy)phenyl]-7-methyl-2-oxo-1-oxa-3-azaspiro[4.5]dec-7-yl}methyl)-1H-benzimidazole-6-carbonitril

Guidance literature:: In 1,4-dioxane; at 120 ℃; for 17h; Sealed tube;
DOI:10.1021/acsmedchemlett.9b00274

Reference yield:

: 1416324-25-8
(2R,3R)-7-methyl-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-6-ene

: 1416323-43-7
1-({(5S,7S)-3-[4-(ethyloxy)phenyl]-7-methyl-2-oxo-1-oxa-3-azaspiro[4.5]dec-7-yl}methyl)-1H-benzimidazole-6-carbonitril

Guidance literature:: Multi-step reaction with 10 steps

1: zinc; copper(II) sulfate; iodine; hydrogenchloride / diethyl ether / 1.5 h / Reflux

2: hydrogen bromide / water; methanol / 24 h / 20 °C

3: potassium phtalimide / 1-methyl-pyrrolidin-2-one / 120 h / 120 °C

4: hydrazine / methanol / 2 h / Reflux

5: potassium carbonate / acetonitrile; dichloromethane / 2 h / 40 °C

6: iron; formic acid / ethyl acetate; methanol / 3.5 h / 64 °C

7: formic acid / 18 h / 70 °C

8: potassium tert-butylate / dimethyl sulfoxide / 1 h / 20 °C

9: methanol / 24 h / 120 °C / Sealed tube

10: 1,4-dioxane / 17 h / 120 °C / Sealed tube

With hydrogenchloride; formic acid; potassium tert-butylate; hydrogen bromide; iodine; iron; potassium carbonate; potassium phtalimide; copper(II) sulfate; hydrazine; zinc; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetonitrile;
DOI:10.1021/acsmedchemlett.9b00274

Reference yield:

: 1416324-26-9
(1S,4'R,5'R,6R)-6-methyl-4',5'-diphenylspiro[bicyclo[4.1.0]heptane-2,2'-[1,3]dioxolane]

: 1416323-43-7
1-({(5S,7S)-3-[4-(ethyloxy)phenyl]-7-methyl-2-oxo-1-oxa-3-azaspiro[4.5]dec-7-yl}methyl)-1H-benzimidazole-6-carbonitril

Guidance literature:: Multi-step reaction with 11 steps

1: hydrogen bromide / water; methanol / 24 h / 20 °C

2: potassium phtalimide / 1-methyl-pyrrolidin-2-one / 120 h / 120 °C

3: hydrazine / methanol / 2 h / Reflux

4: potassium carbonate / acetonitrile; dichloromethane / 2 h / 40 °C

5: iron; formic acid / ethyl acetate; methanol / 3.5 h / 64 °C

6: formic acid / 18 h / 70 °C

7: potassium tert-butylate / dimethyl sulfoxide / 1 h / 20 °C

8: trifluoroacetic acid; water / N,N-dimethyl-formamide / 20.5 h / 10 - 20 °C

9: dmap; p-toluenesulfonyl chloride; triethylamine / dichloromethane / 18 h / 5 - 20 °C

10: methanol / 24 h / 120 °C / Sealed tube

11: 1,4-dioxane / 17 h / 120 °C / Sealed tube

With dmap; formic acid; potassium tert-butylate; water; hydrogen bromide; iron; potassium carbonate; potassium phtalimide; triethylamine; p-toluenesulfonyl chloride; trifluoroacetic acid; hydrazine; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/acsmedchemlett.9b00274