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

Base Information

• Chemical Name: tert-butyl trans-[4-(6-amidinobenzo[b]thiophen-2-carboxamido)cyclohexyloxy]acetate
• CAS No.: 174775-29-2
• Molecular Formula: C₂₂H₂₉N₃O₄S
• Molecular Weight: 431.556

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

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

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

There total 11 articles about tert-butyl trans-[4-(6-amidinobenzo[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:

ethyl 6-nitrobenzo[b]thiophen-2-carboxylate (259150-06-6) → tert-butyl trans-[4-(6-amidinobenzo[b]thiophen-2-carboxamido)cyclohexyloxy]acetate (174775-29-2)

Guidance literature:

Multi-step reaction with 7 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

5.1: H₂S; TEA / pyridine / 18 h / 20 °C

6.1: acetone / 0.67 h / Heating

7.1: ammonium acetate / methanol / 3 h / Heating

With ammonium acetate; hydrogenchloride; lithium hydroxide; TEA; hydrogen sulfide; hydrogen; benzotriazol-1-ol; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; N,N-dimethyl-formamide; acetone; 1.1: Reduction / 2.1: Diazotization / 2.2: Sandmeyer reaction / 3.1: Hydrolysis / 4.1: coupling / 5.1: Addition / 6.1: Methylation / 7.1: Substitution;

DOI:10.1248/cpb.47.1694

Reference yield:

{4-[(6-methylsulfanylcarbonimidoyl-benzo[b]thiophene-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester → tert-butyl trans-[4-(6-amidinobenzo[b]thiophen-2-carboxamido)cyclohexyloxy]acetate (174775-29-2)

Guidance literature:

With ammonium acetate; In methanol; for 3h; Heating;

DOI:10.1248/cpb.47.1694

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → tert-butyl trans-[4-(6-amidinobenzo[b]thiophen-2-carboxamido)cyclohexyloxy]acetate (174775-29-2)

Guidance literature:

Multi-step reaction with 6 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

4: H₂S; TEA / pyridine / 18 h / 20 °C

5: acetone / 0.67 h / Heating

6: ammonium acetate / methanol / 3 h / Heating

With ammonium acetate; sodium hydroxide; TEA; hydrogen sulfide; tetra(n-butyl)ammonium hydrogensulfate; ammonium chloride; benzotriazol-1-ol; In pyridine; methanol; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 1: Substitution / 2: deprotection / 3: coupling / 4: Addition / 5: Methylation / 6: Substitution;

DOI:10.1248/cpb.47.1694

upstream raw materials:

bromoacetic acid tert-butyl ester

6-Cyanbenzothiophen-2-carbonsaeure

6-Cyanbenzothiophen-2-carbonsaeure-ethylester

ethyl 6-amino-1-benzo[b]thiophene-2-carboxylate

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