tert-butyl trans-[4-(6-cyanobenzo[b]thiophen-2-carboxamido)cyclohexyloxy]acetate

Base Information

• Chemical Name: tert-butyl trans-[4-(6-cyanobenzo[b]thiophen-2-carboxamido)cyclohexyloxy]acetate
• CAS No.: 174775-28-1
• Molecular Formula: C₂₂H₂₆N₂O₄S
• Molecular Weight: 414.525

Synonyms:tert-butyl trans-[4-(6-cyanobenzo[b]thiophen-2-carboxamido)cyclohexyloxy]acetate

Chemical Property of tert-butyl trans-[4-(6-cyanobenzo[b]thiophen-2-carboxamido)cyclohexyloxy]acetate

Chemical Property:

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Technology Process of tert-butyl trans-[4-(6-cyanobenzo[b]thiophen-2-carboxamido)cyclohexyloxy]acetate

There total 7 articles about tert-butyl trans-[4-(6-cyanobenzo[b]thiophen-2-carboxamido)cyclohexyloxy]acetate 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: 58.0%

6-Cyanbenzothiophen-2-carbonsaeure (105212-28-0) + tert-butyl trans-(4-aminocyclohexyloxy)acetate (160132-94-5) → tert-butyl trans-[4-(6-cyanobenzo[b]thiophen-2-carboxamido)cyclohexyloxy]acetate (174775-28-1)

Guidance literature:

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

DOI:10.1248/cpb.47.1694

Reference yield:

ethyl 6-nitrobenzo[b]thiophen-2-carboxylate (259150-06-6) → tert-butyl trans-[4-(6-cyanobenzo[b]thiophen-2-carboxamido)cyclohexyloxy]acetate (174775-28-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: H₂ / 10 percent Pd/C / ethanol / 15 h / 20 °C

2.1: 12N aq. HCl; NaNO₂ / tetrahydrofuran / 0.33 h / 2 - 3 °C

2.2: KCN / 3.5 h / 3 - 50 °C

3.1: aq. LiOH / tetrahydrofuran / 1 h / 20 °C

4.1: 58 percent / HOBt; EDI / dimethylformamide / 18 h / 20 °C

With hydrogenchloride; lithium hydroxide; hydrogen; benzotriazol-1-ol; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Diazotization / 2.2: Sandmeyer reaction / 3.1: Hydrolysis / 4.1: coupling;

DOI:10.1248/cpb.47.1694

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → tert-butyl trans-[4-(6-cyanobenzo[b]thiophen-2-carboxamido)cyclohexyloxy]acetate (174775-28-1)

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: 58 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

upstream raw materials:

6-Cyanbenzothiophen-2-carbonsaeure

tert-butyl trans-(4-aminocyclohexyloxy)acetate

bromoacetic acid tert-butyl ester

6-Cyanbenzothiophen-2-carbonsaeure-ethylester

Downstream raw materials:

tert-butyl trans-[4-(6-amidinobenzo[b]thiophen-2-carboxamido)cyclohexyloxy]acetate

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