N-((1R,6R)-6-amino-2,2-difluorocyclohexyl)-4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophene-2-carboxamide

Base Information

Chemical Name:N-((1R,6R)-6-amino-2,2-difluorocyclohexyl)-4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophene-2-carboxamide
CAS No.:1314893-26-9
Molecular Formula:C₁₈H₁₈ClF₂N₅OS
Molecular Weight:425.89
Hs Code.:

Synonyms:N-((1R,6R)-6-amino-2,2-difluorocyclohexyl)-4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophene-2-carboxamide

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Chemical Property of N-((1R,6R)-6-amino-2,2-difluorocyclohexyl)-4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophene-2-carboxamide

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Technology Process of N-((1R,6R)-6-amino-2,2-difluorocyclohexyl)-4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophene-2-carboxamide

There total 12 articles about N-((1R,6R)-6-amino-2,2-difluorocyclohexyl)-4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophene-2-carboxamide 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:

: 1314894-07-9
tert-butyl (1R,2R)-2-({[4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophen-2-yl]carbonyl}amino)-3,3-difluorocyclohexylcarbamate

: 1314893-26-9
N-((1R,6R)-6-amino-2,2-difluorocyclohexyl)-4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophene-2-carboxamide

Guidance literature:: tert-butyl (1R,2R)-2-({[4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophen-2-yl]carbonyl}amino)-3,3-difluorocyclohexylcarbamate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 16h;

With sodium hydrogencarbonate; In water;

Reference yield:

: 1109284-37-8
tert-butyl N-[(1R,2R)-2-amino-3,3-difluorocyclohexyl]carbamate

: 1314894-05-7
4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophene-2-carboxylic acid

: 1314893-26-9
N-((1R,6R)-6-amino-2,2-difluorocyclohexyl)-4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophene-2-carboxamide

Guidance literature:: tert-butyl N-[(1R,2R)-2-amino-3,3-difluorocyclohexyl]carbamate; 4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophene-2-carboxylic acid; With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; at 20 ℃;

With trifluoroacetic acid; In dichloromethane;
DOI:10.1016/j.bmcl.2016.02.003

Reference yield:

: 1314893-92-9
3-bromo-6-chloropyrazolo[1,5-a]pyrimidine

: 1314893-26-9
N-((1R,6R)-6-amino-2,2-difluorocyclohexyl)-4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophene-2-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / 100 °C / Inert atmosphere

2.1: potassium hydroxide; water / tetrahydrofuran; methanol / 3 h / 60 °C

3.1: thionyl chloride / 0.5 h / 60 °C

3.2: 0.5 h / 20 °C

4.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C

With thionyl chloride; water; sodium carbonate; trifluoroacetic acid; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;