Technology Process of 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}-2-hydroxyacetamide
There total 9 articles about 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}-2-hydroxyacetamide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
2-((7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-2-ylamino)-2-oxoethyl acetate;
With
water; lithium hydroxide;
In
tetrahydrofuran;
at 20 ℃;
for 1h;
With
hydrogenchloride;
In
tetrahydrofuran; water;
- Guidance literature:
-
Multi-step reaction with 9 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
9.1: water; lithium hydroxide / tetrahydrofuran / 1 h / 20 °C
With
piperidine; pyridine; water; copper diacetate; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; triethylamine; rac-Pro-OH; lithium hydroxide;
In
tetrahydrofuran; ethanol; 2-Methylpentane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
- Guidance literature:
-
Multi-step reaction with 6 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
6.1: water; lithium hydroxide / tetrahydrofuran / 1 h / 20 °C
With
pyridine; water; copper diacetate; hydrazine hydrate; triethylamine; lithium hydroxide;
In
tetrahydrofuran; ethanol; 2-Methylpentane; dichloromethane; ethyl acetate; toluene;