4'-methoxycinnamoyl 2-methyl-3-(dimethylaminomethyl)-A-ring-pyrrole-duocarmycin C₂

Base Information

• Chemical Name: 4'-methoxycinnamoyl 2-methyl-3-(dimethylaminomethyl)-A-ring-pyrrole-duocarmycin C₂
• CAS No.: 205051-16-7
• Molecular Formula: C₂₅H₂₈ClN₃O₃
• Molecular Weight: 453.969

Synonyms:4'-methoxycinnamoyl 2-methyl-3-(dimethylaminomethyl)-A-ring-pyrrole-duocarmycin C₂

Chemical Property of 4'-methoxycinnamoyl 2-methyl-3-(dimethylaminomethyl)-A-ring-pyrrole-duocarmycin C₂

Chemical Property:

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Technology Process of 4'-methoxycinnamoyl 2-methyl-3-(dimethylaminomethyl)-A-ring-pyrrole-duocarmycin C₂

There total 13 articles about 4'-methoxycinnamoyl 2-methyl-3-(dimethylaminomethyl)-A-ring-pyrrole-duocarmycin C₂ 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:

8-O-tert-butyldimethylsilylduocarmycin B2 (129953-15-7) → 4'-methoxycinnamoyl 2-methyl-3-(dimethylaminomethyl)-A-ring-pyrrole-duocarmycin C2 (205051-16-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 5.70 g / K₂CO₃ / 5.67 h / 0 °C

2: 35 percent / NaBH₄ / various solvent(s) / 105 h / 0 °C

3: 71 percent / BF₃*Et₂O / CHCl₃ / 17.5 h / Ambient temperature

4: 99 percent / Pd(PPh₃)4, dimedone / tetrahydrofuran / 1 h / Ambient temperature

5: 60 percent / PhBr / 10 h / 165 °C

6: nBu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

7: NaOMe / methanol / 1 h / Ambient temperature

8: dimethylformamide / 0.83 h

9: 4 N HCl in AcOEt / tetrahydrofuran / 0.75 h / Ambient temperature

10: TFA / 2.17 h / -10 °C

With hydrogenchloride; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bromobenzene; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; potassium carbonate; dimedone; trifluoroacetic acid; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm990094r

Reference yield:

8-O-(tert-butyldimethylsilyl)-2-methyl-3-(benzyloxycarbonyl)-A-ring-pyrrole-duocarmycin B2 (246034-77-5) → 4'-methoxycinnamoyl 2-methyl-3-(dimethylaminomethyl)-A-ring-pyrrole-duocarmycin C2 (205051-16-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / 25 percent aq. HCO₂NH₄ / 10 percent Pd/C / tetrahydrofuran / 0.5 h / Ambient temperature

2: 60 percent / PhBr / 10 h / 165 °C

3: nBu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

4: NaOMe / methanol / 1 h / Ambient temperature

5: dimethylformamide / 0.83 h

6: 4 N HCl in AcOEt / tetrahydrofuran / 0.75 h / Ambient temperature

7: TFA / 2.17 h / -10 °C

With hydrogenchloride; bromobenzene; tetrabutyl ammonium fluoride; ammonium formate; sodium methylate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm990094r

Reference yield:

8-bromomethyl-4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2-methyl-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2-carboxylic acid benzyl ester → 4'-methoxycinnamoyl 2-methyl-3-(dimethylaminomethyl)-A-ring-pyrrole-duocarmycin C2 (205051-16-7)

Guidance literature:

Multi-step reaction with 8 steps

1: BF₃*Et₂O / CHCl₃ / 17.5 h / Ambient temperature

2: 80 percent / 25 percent aq. HCO₂NH₄ / 10 percent Pd/C / tetrahydrofuran / 0.5 h / Ambient temperature

3: 60 percent / PhBr / 10 h / 165 °C

4: nBu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

5: NaOMe / methanol / 1 h / Ambient temperature

6: dimethylformamide / 0.83 h

7: 4 N HCl in AcOEt / tetrahydrofuran / 0.75 h / Ambient temperature

8: TFA / 2.17 h / -10 °C

With hydrogenchloride; bromobenzene; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; ammonium formate; sodium methylate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm990094r

upstream raw materials:

bis-(dimethylamino)methane

2-methyl-A-ring pyrrole-duocarmycin A

8-O-(tert-butyldimethylsilyl)-2-methyl-A-ring-pyrrole-duocarmyicin B₂

8-O-tert-butyldimethylsilylduocarmycin B₂

Downstream raw materials:

C₂₅H₂₇N₃O₃

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