(5R,7S)-5-(4-hydroxyphenyl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid 4-fluoro-benzylamide

Base Information

Chemical Name:(5R,7S)-5-(4-hydroxyphenyl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid 4-fluoro-benzylamide
CAS No.:1429940-08-8
Molecular Formula:C₂₁H₁₈F₄N₄O₂
Molecular Weight:434.393
Hs Code.:

Synonyms:(5R,7S)-5-(4-hydroxyphenyl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid 4-fluoro-benzylamide

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Chemical Property of (5R,7S)-5-(4-hydroxyphenyl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid 4-fluoro-benzylamide

Chemical Property:

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Technology Process of (5R,7S)-5-(4-hydroxyphenyl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid 4-fluoro-benzylamide

There total 8 articles about (5R,7S)-5-(4-hydroxyphenyl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid 4-fluoro-benzylamide 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:

: 1429940-04-4
(5R,7S)-5-(4-hydroxyphenyl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid

: 140-75-0
para-fluorobenzylamine

: 1429940-08-8
(5R,7S)-5-(4-hydroxyphenyl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid 4-fluoro-benzylamide

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 ℃;
DOI:10.1021/ml400071a

Reference yield:

: 5-(4-hydroxyphenyl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid

: 1429940-08-8
(5R,7S)-5-(4-hydroxyphenyl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid 4-fluoro-benzylamide

Guidance literature:: Multi-step reaction with 2 steps

1: Resolution of racemate

2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

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;
DOI:10.1021/ml400071a

Reference yield:

: 99-93-4
4-Hydroxyacetophenone

: 1429940-08-8
(5R,7S)-5-(4-hydroxyphenyl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid 4-fluoro-benzylamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

1.2: 0 - 20 °C

2.1: acetic acid / 110 °C

3.1: sodium tetrahydroborate / ethanol / 3 h / Reflux

4.1: potassium hydroxide / water; ethanol / 80 °C

5.1: Resolution of racemate

6.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

With sodium tetrahydroborate; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium hydroxide; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1021/ml400071a