{4-[(6-cyano-1H-indole-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester

Base Information

• Chemical Name: {4-[(6-cyano-1H-indole-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester
• CAS No.: 174775-27-0
• Molecular Formula: C₂₂H₂₇N₃O₄
• Molecular Weight: 397.474
• Mol file: 174775-27-0.mol

Synonyms:{4-[(6-cyano-1H-indole-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester

Chemical Property of {4-[(6-cyano-1H-indole-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {4-[(6-cyano-1H-indole-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester

There total 5 articles about {4-[(6-cyano-1H-indole-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester 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: 89.0%

6-cyano-1H-indole-2-carboxylic acid (85864-09-1) + tert-butyl trans-(4-aminocyclohexyloxy)acetate (160132-94-5) → {4-[(6-cyano-1H-indole-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester (174775-27-0)

Guidance literature:

With benzotriazol-1-ol; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1248/cpb.47.1694

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → {4-[(6-cyano-1H-indole-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester (174775-27-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 45 percent / n-Bu₄NHSO₄; aq. NaOH / toluene / 15 h / 20 °C

2: 57 percent / aq. NH₄Cl / 2-methyl-propan-2-ol / 2 h / Heating

3: 89 percent / HOBt; EDI / dimethylformamide / 18 h / 20 °C

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; ammonium chloride; benzotriazol-1-ol; In N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1: Substitution / 2: deprotection / 3: coupling;

DOI:10.1248/cpb.47.1694

Reference yield:

ethyl 6-cyano-1H-indole-2-carboxylate (104291-81-8) → {4-[(6-cyano-1H-indole-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester (174775-27-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 59 percent / aq. LiOH / tetrahydrofuran / 1 h / 20 °C

2: 89 percent / HOBt; EDI / dimethylformamide / 18 h / 20 °C

With lithium hydroxide; benzotriazol-1-ol; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Hydrolysis / 2: coupling;

DOI:10.1248/cpb.47.1694

upstream raw materials:

6-cyano-1H-indole-2-carboxylic acid

tert-butyl trans-(4-aminocyclohexyloxy)acetate

bromoacetic acid tert-butyl ester

ethyl 6-cyano-1H-indole-2-carboxylate

Downstream raw materials:

tert-butyl trans-[4-(6-amidinoindole-2-carboxamido)cyclohexyloxy]acetate