Benzo(1,2-b:4,3-b')dipyrrole-1-carboxylic acid, 3,6,7,8-tetrahydro-8-(bromomethyl)-2-methyl-4-(((4-methyl-1-piperazinyl)carbonyl)oxy)-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester

Base Information

• Chemical Name: Benzo(1,2-b:4,3-b')dipyrrole-1-carboxylic acid, 3,6,7,8-tetrahydro-8-(bromomethyl)-2-methyl-4-(((4-methyl-1-piperazinyl)carbonyl)oxy)-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester
• CAS No.: 134106-78-8
• Molecular Formula: C₃₂H₃₆BrN₅O₈
• Molecular Weight: 698.571
• DSSTox Substance ID: DTXSID60870029
• Mol file: 134106-78-8.mol

Synonyms:134106-78-8;Benzo(1,2-b:4,3-b')dipyrrole-1-carboxylic acid, 3,6,7,8-tetrahydro-8-(bromomethyl)-2-methyl-4-(((4-methyl-1-piperazinyl)carbonyl)oxy)-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester;Benzo[1,2-b:4,3-b']dipyrrole-1-carboxylic acid, 8-(bromomethyl)-3,6,7,8-tetrahydro-2-methyl-4-[[(4-methyl-1-piperazinyl)carbonyl]oxy]-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-, methyl ester;C32H36BrN5O8;DTXSID60870029;C32-H36-Br-N5-O8;LS-34810;Methyl 8-(bromomethyl)-2-methyl-4-[(4-methylpiperazine-1-carbonyl)oxy]-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-1-carboxylate

Chemical Property of Benzo(1,2-b:4,3-b')dipyrrole-1-carboxylic acid, 3,6,7,8-tetrahydro-8-(bromomethyl)-2-methyl-4-(((4-methyl-1-piperazinyl)carbonyl)oxy)-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester

Chemical Property:

• Vapor Pressure: 1.06E-27mmHg at 25°C
• Boiling Point: 829.9°Cat760mmHg
• Flash Point: 455.7°C
• Density: 1.473g/cm³
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 697.17473
• Heavy Atom Count: 46
• Complexity: 1130

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C3C(CN(C3=CC(=C2N1)OC(=O)N4CCN(CC4)C)C(=O)C5=CC6=CC(=C(C(=C6N5)OC)OC)OC)CBr)C(=O)OC

Technology Process of Benzo(1,2-b:4,3-b')dipyrrole-1-carboxylic acid, 3,6,7,8-tetrahydro-8-(bromomethyl)-2-methyl-4-(((4-methyl-1-piperazinyl)carbonyl)oxy)-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester

There total 24 articles about Benzo(1,2-b:4,3-b')dipyrrole-1-carboxylic acid, 3,6,7,8-tetrahydro-8-(bromomethyl)-2-methyl-4-(((4-methyl-1-piperazinyl)carbonyl)oxy)-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester 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: 86.0%

methyl (1S,7R)-1-(bromomethyl)-8-hydroxy-7-methyl-5-[(4-methylpiperazinyl)carbonyloxy]-3-[(5,6,7-tri-methoxy-2-indolyl)carbonyl]-1,2,7,8-tetrahydro-3H-pyrrolo[3,2-e]indole-7-carboxylate → 3-methoxycarbonyl-2-methyl-8-O-(4-methyl-1-piperazinylcarbonyl)duocarmycin B2 (154889-68-6,134106-78-8)

Guidance literature:

With methanesulfonic acid; In 1,2-dichloro-ethane; at 50 ℃; for 5h; Reagent/catalyst; Solvent;

DOI:10.1021/op980038k

Reference yield: 81.0%

methyl (1S,7R,8R)-1-(bromomethyl)-8-hydroxy-7-methyl-5-[(4-methylpiperazinyl)carbonyloxy]-3-[(5,6,7-tri-methoxy-2-indolyl)carbonyl]-1,2,7,8-tetrahydro-3H-pyrrolo[3,2-e]indole-7-carboxylate (160819-29-4) → 3-methoxycarbonyl-2-methyl-8-O-(4-methyl-1-piperazinylcarbonyl)duocarmycin B2 (154889-68-6,134106-78-8)

Guidance literature:

With camphor-10-sulfonic acid; In toluene; at 50 ℃; for 1h;

DOI:10.1248/cpb.44.933

Reference yield: 59.0%

(S)-8-Bromomethyl-2-methyl-4-(piperazine-1-carbonyloxy)-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-1-carboxylic acid methyl ester (192509-09-4) + methyl iodide (74-88-4) → 3-methoxycarbonyl-2-methyl-8-O-(4-methyl-1-piperazinylcarbonyl)duocarmycin B2 (154889-68-6,134106-78-8)

Guidance literature:

With sodium hydrogencarbonate; In methanol; acetone; for 24h; Ambient temperature;

DOI:10.1002/(SICI)1099-1344(199706)39:6<471::AID-JLCR991>3.0.CO;2-K

upstream raw materials:

1-methyl-piperazine

methyl (1S,7R,8R)-1-(bromomethyl)-8-hydroxy-7-methyl-5-[(4-methylpiperazinyl)carbonyloxy]-3-[(5,6,7-tri-methoxy-2-indolyl)carbonyl]-1,2,7,8-tetrahydro-3H-pyrrolo[3,2-e]indole-7-carboxylate

(S)-8-Bromomethyl-2-methyl-4-(piperazine-1-carbonyloxy)-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-1-carboxylic acid methyl ester

methyl iodide

Downstream raw materials:

methyl (1S)-1-(bromomethyl)-7-methyl-5-[(4-methylpiperazinyl)carbonyloxy]-3-[(5,6,7-trimethoxy-2-indolyl)-carbonyl]-1,2-dihydro-3H-pyrrolo[3,2-e]indole-8-carboxylatehydrobromide