5-{4-[2-amino-2-(1H-benzoimidazol-2-yl)-ethyl]-2-bromo-phenyl}-2-tert-butyl-1,1-dioxo-1λ⁶-isothiazolidin-3-one

Base Information

• Chemical Name: 5-{4-[2-amino-2-(1H-benzoimidazol-2-yl)-ethyl]-2-bromo-phenyl}-2-tert-butyl-1,1-dioxo-1λ⁶-isothiazolidin-3-one
• CAS No.: 850320-90-0
• Molecular Formula: C₂₂H₂₅BrN₄O₃S
• Molecular Weight: 505.435

Synonyms:5-{4-[2-amino-2-(1H-benzoimidazol-2-yl)-ethyl]-2-bromo-phenyl}-2-tert-butyl-1,1-dioxo-1λ⁶-isothiazolidin-3-one

Chemical Property of 5-{4-[2-amino-2-(1H-benzoimidazol-2-yl)-ethyl]-2-bromo-phenyl}-2-tert-butyl-1,1-dioxo-1λ⁶-isothiazolidin-3-one

Chemical Property:

Purity/Quality:

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Technology Process of 5-{4-[2-amino-2-(1H-benzoimidazol-2-yl)-ethyl]-2-bromo-phenyl}-2-tert-butyl-1,1-dioxo-1λ⁶-isothiazolidin-3-one

There total 11 articles about 5-{4-[2-amino-2-(1H-benzoimidazol-2-yl)-ethyl]-2-bromo-phenyl}-2-tert-butyl-1,1-dioxo-1λ⁶-isothiazolidin-3-one 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%

2-{2-[3-bromo-4-(2-tert-butyl-1,1,3-trioxo-1λ6-isothiazolidin-5-yl)-phenyl]-1-tert-butoxycarbonylamino-ethyl}-benzoimidazole-1-carboxylic acid tert-butyl ester (850320-89-7) → 5-{4-[2-amino-2-(1H-benzoimidazol-2-yl)-ethyl]-2-bromo-phenyl}-2-tert-butyl-1,1-dioxo-1λ6-isothiazolidin-3-one (850320-90-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2006.10.079

Reference yield:

3-(3-bromo-4-iodo-phenyl)-2-tert-butoxycarbonylamino-propionic acid (850321-49-2) → 5-{4-[2-amino-2-(1H-benzoimidazol-2-yl)-ethyl]-2-bromo-phenyl}-2-tert-butyl-1,1-dioxo-1λ6-isothiazolidin-3-one (850320-90-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: BOPCl; i-Pr₂NEt / dimethylformamide / 2 h / 20 °C

1.2: AcOH / 2 h / 40 °C

2.1: NaOH / H₂O; tetrahydrofuran / 2 h / 35 °C

3.1: 34 percent / Pd(OAc)2; Bu₄NCl; Et₃N / dimethylformamide / 2.5 h / 70 °C

4.1: 78 percent / L-Selectride / tetrahydrofuran / 0.17 h / -78 °C

5.1: 58 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

With palladium diacetate; sodium hydroxide; tetrabutyl-ammonium chloride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; L-Selectride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 3.1: Heck coupling;

DOI:10.1016/j.bmcl.2006.10.079

Reference yield:

3-(3-bromo-4-iodo-phenyl)-2-tert-butoxycarbonylamino-propionic acid benzyl ester (850320-85-3) → 5-{4-[2-amino-2-(1H-benzoimidazol-2-yl)-ethyl]-2-bromo-phenyl}-2-tert-butyl-1,1-dioxo-1λ6-isothiazolidin-3-one (850320-90-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaOH / H₂O; acetonitrile / 2 h / 20 °C

2.1: BOPCl; i-Pr₂NEt / dimethylformamide / 2 h / 20 °C

2.2: AcOH / 2 h / 40 °C

3.1: NaOH / H₂O; tetrahydrofuran / 2 h / 35 °C

4.1: 34 percent / Pd(OAc)2; Bu₄NCl; Et₃N / dimethylformamide / 2.5 h / 70 °C

5.1: 78 percent / L-Selectride / tetrahydrofuran / 0.17 h / -78 °C

6.1: 58 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

With palladium diacetate; sodium hydroxide; tetrabutyl-ammonium chloride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; L-Selectride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 4.1: Heck coupling;

DOI:10.1016/j.bmcl.2006.10.079

upstream raw materials:

2-{2-[3-bromo-4-(2-tert-butyl-1,1,3-trioxo-1λ⁶-isothiazolidin-5-yl)-phenyl]-1-tert-butoxycarbonylamino-ethyl}-benzoimidazole-1-carboxylic acid tert-butyl ester

3-(3-bromo-4-iodo-phenyl)-2-tert-butoxycarbonylamino-propionic acid

3-(3-bromo-4-iodo-phenyl)-2-tert-butoxycarbonylamino-propionic acid benzyl ester

3-(4-amino-3-bromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid benzyl ester

Downstream raw materials:

5-{4-[2-(1H-benzoimidazol-2-yl)-2-(benzothiazol-2-ylamino)-ethyl]-2-bromo-phenyl}-1,1-dioxo-1λ⁶-isothiazolidin-3-one

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