5-Bromo-thiophene-2-carboxylic acid {(S)-1-[(R)-3-(4,4-dimethyl-cyclohexylamino)-pyrrolidine-1-carbonyl]-pyrrolidin-3-yl}-methyl-amide

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Chemical Name:5-Bromo-thiophene-2-carboxylic acid {(S)-1-[(R)-3-(4,4-dimethyl-cyclohexylamino)-pyrrolidine-1-carbonyl]-pyrrolidin-3-yl}-methyl-amide
CAS No.:911398-53-3
Molecular Formula:C₂₃H₃₅BrN₄O₂S
Molecular Weight:511.526
Hs Code.:

Synonyms:5-Bromo-thiophene-2-carboxylic acid {(S)-1-[(R)-3-(4,4-dimethyl-cyclohexylamino)-pyrrolidine-1-carbonyl]-pyrrolidin-3-yl}-methyl-amide

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Chemical Property of 5-Bromo-thiophene-2-carboxylic acid {(S)-1-[(R)-3-(4,4-dimethyl-cyclohexylamino)-pyrrolidine-1-carbonyl]-pyrrolidin-3-yl}-methyl-amide

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Technology Process of 5-Bromo-thiophene-2-carboxylic acid {(S)-1-[(R)-3-(4,4-dimethyl-cyclohexylamino)-pyrrolidine-1-carbonyl]-pyrrolidin-3-yl}-methyl-amide

There total 9 articles about 5-Bromo-thiophene-2-carboxylic acid {(S)-1-[(R)-3-(4,4-dimethyl-cyclohexylamino)-pyrrolidine-1-carbonyl]-pyrrolidin-3-yl}-methyl-amide 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: 69.0%

: 764722-84-1
5-Bromo-thiophene-2-carboxylic acid [(S)-1-((R)-3-amino-pyrrolidine-1-carbonyl)-pyrrolidin-3-yl]-methyl-amide

: 4255-62-3
4,4-dimethylcyclohexane-1-one

: 911398-53-3
5-Bromo-thiophene-2-carboxylic acid {(S)-1-[(R)-3-(4,4-dimethyl-cyclohexylamino)-pyrrolidine-1-carbonyl]-pyrrolidin-3-yl}-methyl-amide

Guidance literature:: With sodium tris(acetoxy)borohydride; In methanol; at 20 ℃; for 18h;
DOI:10.1016/j.bmcl.2006.06.049

Reference yield:

: 169750-00-9
(S)-1-benzyl-3-[[N-(t-butoxycarbonyl)]-N-methylamino]pyrrolidine

: 911398-53-3
5-Bromo-thiophene-2-carboxylic acid {(S)-1-[(R)-3-(4,4-dimethyl-cyclohexylamino)-pyrrolidine-1-carbonyl]-pyrrolidin-3-yl}-methyl-amide

Guidance literature:: Multi-step reaction with 7 steps

1: 76 percent / ammonium formate / Pd/C / ethanol / 2 h / Heating

2: 68 percent / TEA / tetrahydrofuran / 2 h / 0 - 20 °C

3: 66 percent / TEA / dimethylformamide / 2.5 h / 90 °C

4: 100 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

5: 85 percent / EDCI; HOBt; TEA / CH₂Cl₂ / 18 h / 20 °C

6: K₂CO₃ / ethanol; H₂O / 16 h / 80 °C

7: 69 percent / Na(OAc)3BH / methanol / 18 h / 20 °C

With TEA; ammonium formate; sodium tris(acetoxy)borohydride; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2006.06.049

Reference yield:

: 169749-99-9
(3S)-(-)-1-benzyl-3-(methylamino)pyrrolidine

: 911398-53-3
5-Bromo-thiophene-2-carboxylic acid {(S)-1-[(R)-3-(4,4-dimethyl-cyclohexylamino)-pyrrolidine-1-carbonyl]-pyrrolidin-3-yl}-methyl-amide

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / TEA / CH₂Cl₂ / 2 h / 20 °C

2: 76 percent / ammonium formate / Pd/C / ethanol / 2 h / Heating

3: 68 percent / TEA / tetrahydrofuran / 2 h / 0 - 20 °C

4: 66 percent / TEA / dimethylformamide / 2.5 h / 90 °C

5: 100 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

6: 85 percent / EDCI; HOBt; TEA / CH₂Cl₂ / 18 h / 20 °C

7: K₂CO₃ / ethanol; H₂O / 16 h / 80 °C

8: 69 percent / Na(OAc)3BH / methanol / 18 h / 20 °C

With TEA; ammonium formate; sodium tris(acetoxy)borohydride; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2006.06.049