AT-406

Base Information

• Chemical Name: AT-406
• CAS No.: 1071992-57-8
• Molecular Formula: C32H43N5O4.HCl
• Molecular Weight: 598.17600
• Mol file: 1071992-57-8.mol

Synonyms:AT-406;AT-406(HCl);AT-406 (hydrochloride);Xevinapant hydrochloride;(5S,8S,10aR)-N-(Diphenylmethyl)decahydro-5-[[(2S)-2-(methylamino)-1-oxopropyl]amino]-3-(3-methyl-1-oxobutyl)-6-oxo-pyrrolo[1,2-a][1,5]diazocine-8-carboxamide hydrochloride (1:1)

Chemical Property of AT-406

Chemical Property:

• PSA: 110.85000
• LogP: 4.47340

Purity/Quality:

98%,99%, ^*data from raw suppliers

AT-406 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of AT-406

There total 17 articles about AT-406 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:

1-tert-butyl 2-methyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate (195964-54-6) → N1-[(5S,8S,10aR)-8-[N-(1,1-diphenylmethyl)carbamoyl]-3-(3-methylbutyryl)-6-oxoperhydropyrrolo[1,2-a][1,5]diazocin-5-yl]-N2-methyl-L-alaninamide hydrochloride (1071992-57-8)

Guidance literature:

Multi-step reaction with 12 steps

1: boron trifluoride diethyl etherate / diethyl ether / -78 °C

2: hydrogenchloride / acetonitrile; 1,4-dioxane

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane

4: ozone

5: hydrogen; palladium on activated charcoal / isopropyl alcohol

6: sodium tris(acetoxy)borohydride / tetrahydrofuran

7: N-ethyl-N,N-diisopropylamine / dichloromethane

8: lithium hydroxide / 1,4-dioxane; water

9: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane

10: hydrogenchloride / 1,4-dioxane; methanol

11: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane

12: hydrogenchloride / 1,4-dioxane; methanol

With hydrogenchloride; palladium on activated charcoal; boron trifluoride diethyl etherate; hydrogen; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; isopropyl alcohol; acetonitrile;

DOI:10.1358/dof.2017.042.12.2702829

Reference yield:

(2S)-5-allyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (195964-65-9) → N1-[(5S,8S,10aR)-8-[N-(1,1-diphenylmethyl)carbamoyl]-3-(3-methylbutyryl)-6-oxoperhydropyrrolo[1,2-a][1,5]diazocin-5-yl]-N2-methyl-L-alaninamide hydrochloride (1071992-57-8)

Guidance literature:

Multi-step reaction with 11 steps

1: hydrogenchloride / acetonitrile; 1,4-dioxane

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane

3: ozone

4: hydrogen; palladium on activated charcoal / isopropyl alcohol

5: sodium tris(acetoxy)borohydride / tetrahydrofuran

6: N-ethyl-N,N-diisopropylamine / dichloromethane

7: lithium hydroxide / 1,4-dioxane; water

8: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane

9: hydrogenchloride / 1,4-dioxane; methanol

10: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane

11: hydrogenchloride / 1,4-dioxane; methanol

With hydrogenchloride; palladium on activated charcoal; hydrogen; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; isopropyl alcohol; acetonitrile;

DOI:10.1358/dof.2017.042.12.2702829

Reference yield:

5-allyloxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride (637355-27-2) → N1-[(5S,8S,10aR)-8-[N-(1,1-diphenylmethyl)carbamoyl]-3-(3-methylbutyryl)-6-oxoperhydropyrrolo[1,2-a][1,5]diazocin-5-yl]-N2-methyl-L-alaninamide hydrochloride (1071992-57-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane

2: ozone

3: hydrogen; palladium on activated charcoal / isopropyl alcohol

4: sodium tris(acetoxy)borohydride / tetrahydrofuran

5: N-ethyl-N,N-diisopropylamine / dichloromethane

6: lithium hydroxide / 1,4-dioxane; water

7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane

8: hydrogenchloride / 1,4-dioxane; methanol

9: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane

10: hydrogenchloride / 1,4-dioxane; methanol

With hydrogenchloride; palladium on activated charcoal; hydrogen; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; isopropyl alcohol;

DOI:10.1358/dof.2017.042.12.2702829

upstream raw materials:

1-tert-butyl 2-methyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate

(2S)-5-allyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

5-allyloxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride

L-Pyroglutamic acid