(6S)-7-[(4R)-1-{[(5R,6S)-5-(4-chloro-3-fluorophenyl)-6-(6-chloropyridin-3-yl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-4-fluoro-L-prolyl]-6-methyl-4-(trifluoroacetyl)-4,7-diazaspiro[2.5]octane

Base Information

• Chemical Name: (6S)-7-[(4R)-1-{[(5R,6S)-5-(4-chloro-3-fluorophenyl)-6-(6-chloropyridin-3-yl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-4-fluoro-L-prolyl]-6-methyl-4-(trifluoroacetyl)-4,7-diazaspiro[2.5]octane
• CAS No.: 1235576-27-8
• Molecular Formula: C₃₅H₃₅Cl₂F₅N₆O₃S
• Molecular Weight: 785.665

Synonyms:(6S)-7-[(4R)-1-{[(5R,6S)-5-(4-chloro-3-fluorophenyl)-6-(6-chloropyridin-3-yl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-4-fluoro-L-prolyl]-6-methyl-4-(trifluoroacetyl)-4,7-diazaspiro[2.5]octane

Chemical Property of (6S)-7-[(4R)-1-{[(5R,6S)-5-(4-chloro-3-fluorophenyl)-6-(6-chloropyridin-3-yl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-4-fluoro-L-prolyl]-6-methyl-4-(trifluoroacetyl)-4,7-diazaspiro[2.5]octane

Chemical Property:

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Technology Process of (6S)-7-[(4R)-1-{[(5R,6S)-5-(4-chloro-3-fluorophenyl)-6-(6-chloropyridin-3-yl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-4-fluoro-L-prolyl]-6-methyl-4-(trifluoroacetyl)-4,7-diazaspiro[2.5]octane

There total 15 articles about (6S)-7-[(4R)-1-{[(5R,6S)-5-(4-chloro-3-fluorophenyl)-6-(6-chloropyridin-3-yl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-4-fluoro-L-prolyl]-6-methyl-4-(trifluoroacetyl)-4,7-diazaspiro[2.5]octane 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: 85.0%

(5R,6S)-5-(4-Chloro-3-fluorophenyl)-6-(6-chloropyridin-3-yl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole-2-carboxylic acid (1033719-23-1) + (6S)-7-[(4R)-4-fluoro-L-prolyl]-6-methyl-4-(trifluoroacetyl)-4,7-diazaspiro[2.5]octane (1235576-45-0) → (6S)-7-[(4R)-1-{[(5R,6S)-5-(4-chloro-3-fluorophenyl)-6-(6-chloropyridin-3-yl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-4-fluoro-L-prolyl]-6-methyl-4-(trifluoroacetyl)-4,7-diazaspiro[2.5]octane (1235576-27-8)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

Reference yield:

3-acetyl-6-chloropyridine (55676-22-7) → (6S)-7-[(4R)-1-{[(5R,6S)-5-(4-chloro-3-fluorophenyl)-6-(6-chloropyridin-3-yl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-4-fluoro-L-prolyl]-6-methyl-4-(trifluoroacetyl)-4,7-diazaspiro[2.5]octane (1235576-27-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: ammonium hydroxide; ammonium chloride / methanol / 72 h / 20 °C

1.2: 2 h / Reflux; Cooling with ice

2.1: triethylamine / tetrahydrofuran / 36 h / Reflux

2.2: Reflux

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Cooling with ice

3.2: Cooling with ice

4.1: sulfur trioxide pyridine complex; triethylamine / dimethyl sulfoxide / 2 h / 20 °C

5.1: tetrahydrofuran / 1 h / Cooling with ice

6.1: acetic anhydride; dimethyl sulfoxide / 18 h / 20 °C / Cooling with ice

7.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C / Cooling with ice

8.1: SULFAMIDE; 1,8-diazabicyclo[5.4.0]undec-7-ene / 1,4-dioxane / 42 h / 95 °C / Molecular sieve

9.1: sodium tetrahydroborate / ethanol / 2 h / Cooling with ice

10.1: ethylenediamine / 1,4-dioxane / 18 h / 100 °C

11.1: L-Tartaric acid / ethanol / 0.5 h / 110 °C / Reflux

12.1: ethanol / 20 h / Reflux

13.1: ethanol / 16 h / Reflux

14.1: water; sodium hydroxide / ethanol / 16 h / 60 °C

14.2: Cooling with ice

15.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 24 h / 20 °C

With hydrogenchloride; ammonium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; L-Tartaric acid; water; sulfur trioxide pyridine complex; acetic anhydride; SULFAMIDE; ammonium chloride; benzotriazol-1-ol; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethylenediamine; triethylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

(1R,2S)-1-(4-Chloro-3-fluorophenyl)-2-(6-chloropyridin-3-yl)propane-1,2-diamine (1033719-19-5) → (6S)-7-[(4R)-1-{[(5R,6S)-5-(4-chloro-3-fluorophenyl)-6-(6-chloropyridin-3-yl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-4-fluoro-L-prolyl]-6-methyl-4-(trifluoroacetyl)-4,7-diazaspiro[2.5]octane (1235576-27-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ethanol / 20 h / Reflux

2.1: ethanol / 16 h / Reflux

3.1: water; sodium hydroxide / ethanol / 16 h / 60 °C

3.2: Cooling with ice

4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 24 h / 20 °C

With water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In ethanol; N,N-dimethyl-formamide;

upstream raw materials:

3-acetyl-6-chloropyridine

(1R,2S)-1-(4-Chloro-3-fluorophenyl)-2-(6-chloropyridin-3-yl)propane-1,2-diamine

Ethyl (5R,6S)-5-(4-Chloro-3-fluorophenyl)-6-(6-chloropyridin-3-yl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole-2-carboxylate

(5R,6S)-5-(4-Chloro-3-fluorophenyl)-6-(6-chloropyridin-3-yl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole-2-carboxylic acid

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