(S)-tert-butyl 1-(1-cyano-2-(4-(6-isopropyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)phenyl)ethylcarbamoyl)cyclohexylcarbamate

Base Information

• Chemical Name: (S)-tert-butyl 1-(1-cyano-2-(4-(6-isopropyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)phenyl)ethylcarbamoyl)cyclohexylcarbamate
• CAS No.: 1352152-95-4
• Molecular Formula: C₃₁H₃₉N₅O₄
• Molecular Weight: 545.682
• Mol file: 1352152-95-4.mol

Synonyms:(S)-tert-butyl 1-(1-cyano-2-(4-(6-isopropyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)phenyl)ethylcarbamoyl)cyclohexylcarbamate

Chemical Property of (S)-tert-butyl 1-(1-cyano-2-(4-(6-isopropyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)phenyl)ethylcarbamoyl)cyclohexylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-tert-butyl 1-(1-cyano-2-(4-(6-isopropyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)phenyl)ethylcarbamoyl)cyclohexylcarbamate

There total 10 articles about (S)-tert-butyl 1-(1-cyano-2-(4-(6-isopropyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)phenyl)ethylcarbamoyl)cyclohexylcarbamate 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:

N-Boc-4-I-Phe-OH (103882-09-3,62129-44-6) → (S)-tert-butyl 1-(1-cyano-2-(4-(6-isopropyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)phenyl)ethylcarbamoyl)cyclohexylcarbamate (1352152-95-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethylmorpholine; / N,N-dimethyl-formamide / 0.5 h / 20 °C

1.2: 16 h / 0 - 28 °C

2.1: trifluoroacetic acid / dichloromethane / 50 h

3.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 2 h / 17 - 28 °C

4.1: potassium acetate / dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / acetonitrile; water / 4 h / Reflux

5.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 0.5 h / 80 °C / Inert atmosphere

6.1: Burgess Reagent / dichloromethane / 18 h / 17 - 28 °C / Inert atmosphere

With N-ethylmorpholine;; Burgess Reagent; potassium acetate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

(S)-tert-butyl 1-(1-amino-3-(4-(6-isopropyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)cyclohexylcarbamate (1352152-94-3) → (S)-tert-butyl 1-(1-cyano-2-(4-(6-isopropyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)phenyl)ethylcarbamoyl)cyclohexylcarbamate (1352152-95-4)

Guidance literature:

With Burgess Reagent; In dichloromethane; at 17 - 28 ℃; for 18h; Inert atmosphere;

Reference yield:

(S)-2-amino-3-(4-iodophenyl)propionamamide (97964-72-2) → (S)-tert-butyl 1-(1-cyano-2-(4-(6-isopropyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)phenyl)ethylcarbamoyl)cyclohexylcarbamate (1352152-95-4)

Guidance literature:

Multi-step reaction with 4 steps

1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 2 h / 17 - 28 °C

2: potassium acetate / dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / acetonitrile; water / 4 h / Reflux

3: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 0.5 h / 80 °C / Inert atmosphere

4: Burgess Reagent / dichloromethane / 18 h / 17 - 28 °C / Inert atmosphere

With Burgess Reagent; potassium acetate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

N-Boc-4-I-Phe-OH

(S)-2-amino-3-(4-iodophenyl)propionamamide

5-bromo-3-methylpyridine-2-carboxylic acid methyl ester

5-bromo-3-methylpyridine-2-carboxylic acid

Refernces