N₂-acetyl-N-{(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro [1,2,4]triazolo[1,5-a]pyrimidin-2-yl}glycinamide

Base Information

• Chemical Name: N₂-acetyl-N-{(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro [1,2,4]triazolo[1,5-a]pyrimidin-2-yl}glycinamide
• CAS No.: 1234619-58-9
• Molecular Formula: C₂₅H₁₉F₃N₈O₂
• Molecular Weight: 520.473

Synonyms:N₂-acetyl-N-{(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro [1,2,4]triazolo[1,5-a]pyrimidin-2-yl}glycinamide

Chemical Property of N₂-acetyl-N-{(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro [1,2,4]triazolo[1,5-a]pyrimidin-2-yl}glycinamide

Chemical Property:

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Technology Process of N₂-acetyl-N-{(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro [1,2,4]triazolo[1,5-a]pyrimidin-2-yl}glycinamide

There total 8 articles about N₂-acetyl-N-{(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro [1,2,4]triazolo[1,5-a]pyrimidin-2-yl}glycinamide 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: 65.0%

aceturoyl chloride (72952-59-1) + (7R)-2-amino-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile hydrochloride → N2-acetyl-N-{(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro [1,2,4]triazolo[1,5-a]pyrimidin-2-yl}glycinamide (1234619-58-9)

Guidance literature:

With pyridine; at 20 ℃; for 12h; Inert atmosphere;

Reference yield:

4-cyanobenzaldehyde (105-07-7) → N2-acetyl-N-{(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro [1,2,4]triazolo[1,5-a]pyrimidin-2-yl}glycinamide (1234619-58-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: piperidine; acetic acid / dichloromethane / 18 h / Reflux

2.1: pyridine; rac-Pro-OH / dichloromethane; N,N-dimethyl-formamide / 192 h / Inert atmosphere; Molecular sieve

3.1: toluene-4-sulfonic acid; pyridine / toluene / 1 h / Reflux

4.1: triethylamine; pyridine / toluene / Inert atmosphere; Reflux

5.1: triethylamine; pyridine; copper diacetate / dichloromethane / 36 h / Inert atmosphere; Molecular sieve

5.2: 36 h

5.3: 120 h

6.1: chiral silica gel phase based on the selector poly(N-methacryloyl-L-isoleucine-3-pentylamide) / ethyl acetate; 2-Methylpentane / 24 °C / Resolution of racemate

7.1: hydrazine hydrate / ethanol / 1 h / 85 °C / Inert atmosphere

8.1: pyridine / 12 h / 20 °C / Inert atmosphere

With piperidine; pyridine; copper diacetate; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; triethylamine; rac-Pro-OH; In ethanol; 2-Methylpentane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

Reference yield:

(rac)-2-amino-7-(4-cyanophenyl)-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile (1234620-57-5) → N2-acetyl-N-{(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro [1,2,4]triazolo[1,5-a]pyrimidin-2-yl}glycinamide (1234619-58-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine; pyridine / toluene / Inert atmosphere; Reflux

2.1: triethylamine; pyridine; copper diacetate / dichloromethane / 36 h / Inert atmosphere; Molecular sieve

2.2: 36 h

2.3: 120 h

3.1: chiral silica gel phase based on the selector poly(N-methacryloyl-L-isoleucine-3-pentylamide) / ethyl acetate; 2-Methylpentane / 24 °C / Resolution of racemate

4.1: hydrazine hydrate / ethanol / 1 h / 85 °C / Inert atmosphere

5.1: pyridine / 12 h / 20 °C / Inert atmosphere

With pyridine; copper diacetate; hydrazine hydrate; triethylamine; In ethanol; 2-Methylpentane; dichloromethane; ethyl acetate; toluene;

upstream raw materials:

4-cyanobenzaldehyde

aceturoyl chloride

(rac)-2-amino-7-(4-cyanophenyl)-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile

(rac)-7-(4-cyanophenyl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile

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