5-Benzoylamino-1H-indole-2-carboxylic acid [2-(5-benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carbonyl)-1H-indol-5-yl]-amide

Base Information

• Chemical Name: 5-Benzoylamino-1H-indole-2-carboxylic acid [2-(5-benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carbonyl)-1H-indol-5-yl]-amide
• CAS No.: 101134-52-5
• Molecular Formula: C₄₄H₃₆N₆O₅
• Molecular Weight: 728.807
• Mol file: 101134-52-5.mol

Synonyms:5-Benzoylamino-1H-indole-2-carboxylic acid [2-(5-benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carbonyl)-1H-indol-5-yl]-amide

Chemical Property of 5-Benzoylamino-1H-indole-2-carboxylic acid [2-(5-benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carbonyl)-1H-indol-5-yl]-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Benzoylamino-1H-indole-2-carboxylic acid [2-(5-benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carbonyl)-1H-indol-5-yl]-amide

There total 17 articles about 5-Benzoylamino-1H-indole-2-carboxylic acid [2-(5-benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carbonyl)-1H-indol-5-yl]-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:

4-nitro-1H-indole-2-carboxylic acid ethyl ester (4993-93-5) → 5-Benzoylamino-1H-indole-2-carboxylic acid [2-(5-benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carbonyl)-1H-indol-5-yl]-amide (101134-52-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 83 percent / hydrogen / PtO₂ / ethanol; tetrahydrofuran / 3.25 h / 724.01 Torr

2: 81 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 48 h

3: 97 percent / aq. KOH / methanol; dimethylformamide / 0.5 h

4: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 48 h

5: 51 percent / aq. KOH / dimethylformamide

6: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride

With potassium hydroxide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00398a017

Reference yield:

3-nitro-4-chlorophenol (610-78-6) → 5-Benzoylamino-1H-indole-2-carboxylic acid [2-(5-benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carbonyl)-1H-indol-5-yl]-amide (101134-52-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 96 percent / K₂CO₃ / acetone; dimethylformamide / 64 h / Ambient temperature

2: 77 percent / NaH / dimethylsulfoxide / 24 h / 105 - 115 °C

3: 40 percent / diisobutylaluminum hydride / tetrahydrofuran / 2.3 h / Ambient temperature

4: 69 percent / hydrogen / 84.5percent PtO₂ / ethanol / 2.75 h / 2327.2 Torr

5: 111 g / pyridine / 1.42 h / 5 °C

6: 1.) sodium acetate, 2.) triethylamine / 1.) ethanol, reflux, 20 h, 2.) methylene chloride

7: 64 percent / nitric acid / nitromethane / 0.67 h / 0 °C

8: 81 percent / hydrogen / 84.5percent PtO₂ / tetrahydrofuran; ethanol / 2 h / 2068.6 Torr

9: 1.) sulfuryl chloride, 2.) 1,8-bis(dimethylamino)naphthalene / 1.) methylene chloride, -70 deg C, 45 min, 2.) -70 deg C, 4 h

10: 90 percent / borane-methyl sulfide, 4-Angstroem molecular sieves / tetrahydrofuran / 3 h / Heating

11: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene

12: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride

With pyridine; sulfuryl dichloride; dimethylsulfide borane complex; 4 A molecular sieve; hydrogen; nitric acid; sodium acetate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; platinum(IV) oxide; In tetrahydrofuran; nitromethane; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jm00398a017

Reference yield:

2-[4-(benzyloxy)-2-nitrophenyl]propane-1,3-diol (106014-83-9) → 5-Benzoylamino-1H-indole-2-carboxylic acid [2-(5-benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carbonyl)-1H-indol-5-yl]-amide (101134-52-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 69 percent / hydrogen / 84.5percent PtO₂ / ethanol / 2.75 h / 2327.2 Torr

2: 111 g / pyridine / 1.42 h / 5 °C

3: 1.) sodium acetate, 2.) triethylamine / 1.) ethanol, reflux, 20 h, 2.) methylene chloride

4: 64 percent / nitric acid / nitromethane / 0.67 h / 0 °C

5: 81 percent / hydrogen / 84.5percent PtO₂ / tetrahydrofuran; ethanol / 2 h / 2068.6 Torr

6: 1.) sulfuryl chloride, 2.) 1,8-bis(dimethylamino)naphthalene / 1.) methylene chloride, -70 deg C, 45 min, 2.) -70 deg C, 4 h

7: 90 percent / borane-methyl sulfide, 4-Angstroem molecular sieves / tetrahydrofuran / 3 h / Heating

8: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene

9: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride

With pyridine; sulfuryl dichloride; dimethylsulfide borane complex; 4 A molecular sieve; hydrogen; nitric acid; sodium acetate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; platinum(IV) oxide; In tetrahydrofuran; nitromethane; ethanol; toluene;

DOI:10.1021/jm00398a017

upstream raw materials:

5-(benzyloxy)-1,2,3,6-tetrahydro-8-methylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol

5-<<<5-(benzoylamino)-1H-indol-2-yl>carbonyl>amino>-1H-indole-2-carboxylic acid

3-nitro-4-chlorophenol

4-nitro-1H-indole-2-carboxylic acid ethyl ester

Downstream raw materials:

C₃₇H₂₈N₆O₄

Methanesulfonic acid 3-{5-[(5-benzoylamino-1H-indole-2-carbonyl)-amino]-1H-indole-2-carbonyl}-5-benzyloxy-8-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-e]indol-1-ylmethyl ester