(3-(5-(2-(dimethylamino)ethoxy)-1H-indole-2-carbonyl)-5-nitro-7-((2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)carbamoyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate

Base Information

• Chemical Name: (3-(5-(2-(dimethylamino)ethoxy)-1H-indole-2-carbonyl)-5-nitro-7-((2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)carbamoyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate
• CAS No.: 1363480-05-0
• Molecular Formula: C₄₁H₄₅N₅O₁₀S
• Molecular Weight: 799.902

Synonyms:(3-(5-(2-(dimethylamino)ethoxy)-1H-indole-2-carbonyl)-5-nitro-7-((2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)carbamoyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate

Chemical Property of (3-(5-(2-(dimethylamino)ethoxy)-1H-indole-2-carbonyl)-5-nitro-7-((2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)carbamoyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate

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Technology Process of (3-(5-(2-(dimethylamino)ethoxy)-1H-indole-2-carbonyl)-5-nitro-7-((2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)carbamoyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate

There total 20 articles about (3-(5-(2-(dimethylamino)ethoxy)-1H-indole-2-carbonyl)-5-nitro-7-((2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)carbamoyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate 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: 77.0%

3-(5-(2-(dimethylamino)ethoxy)-1H-indole-2-carbonyl)-1-(hydroxymethyl)-5-nitro-N-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)-2,3-dihydro-1H-benzo[e]indole-7-carboxamide (1363480-01-6) + benzenesulfonyl chloride (1939-99-7) → (3-(5-(2-(dimethylamino)ethoxy)-1H-indole-2-carbonyl)-5-nitro-7-((2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)carbamoyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate (1363480-05-0)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jm201717y

Reference yield:

tert-butyl (6-cyanonaphthalen-2-yl)carbamate (869114-69-2) → (3-(5-(2-(dimethylamino)ethoxy)-1H-indole-2-carbonyl)-5-nitro-7-((2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)carbamoyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate (1363480-05-0)

Guidance literature:

Multi-step reaction with 15 steps

1.1: N-iodo-succinimide; toluene-4-sulfonic acid / acetonitrile / 36 h / 35 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C

2.2: 16 h / 0 - 20 °C

3.1: tri-n-butyl-tin hydride / benzene / 20 °C / Reflux; Inert atmosphere

4.1: acetic acid; zinc / tetrahydrofuran; water / 2 h / Reflux

5.1: dmap; triethylamine / tetrahydrofuran / 2 h / 20 °C

6.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C

7.1: pyridine / 4 h / 0 °C

8.1: sulfuric acid; potassium nitrate / 0.45 h / -10 °C

9.1: dihydrogen peroxide; potassium carbonate / water; dimethyl sulfoxide / 20 °C

10.1: toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 20 °C

11.1: sodium nitrite / trifluoroacetic acid / 0.25 h / 0 - 20 °C

12.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 - 20 °C

13.1: methanol; caesium carbonate / 0.5 h / 0 °C

14.1: toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 2 h / 20 °C

15.1: pyridine / dichloromethane / 1 h / 0 °C

With pyridine; methanol; dmap; N-iodo-succinimide; sulfuric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydride; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; zinc; sodium nitrite; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; trifluoroacetic acid; mineral oil; benzene;

DOI:10.1021/jm201717y

Reference yield:

C14H11IN2 → (3-(5-(2-(dimethylamino)ethoxy)-1H-indole-2-carbonyl)-5-nitro-7-((2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)carbamoyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate (1363480-05-0)

Guidance literature:

Multi-step reaction with 10 steps

1: pyridine / 2 h / 0 °C

2: acetic acid / 48 h / Reflux

3: sulfuric acid; potassium nitrate / 0.45 h / -10 °C

4: dihydrogen peroxide; potassium carbonate / water; dimethyl sulfoxide / 20 °C

5: toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 20 °C

6: sodium nitrite / trifluoroacetic acid / 0.25 h / 0 - 20 °C

7: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 - 20 °C

8: methanol; caesium carbonate / 0.5 h / 0 °C

9: toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 2 h / 20 °C

10: pyridine / dichloromethane / 1 h / 0 °C

With pyridine; methanol; sulfuric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; dihydrogen peroxide; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium nitrate; N-ethyl-N,N-diisopropylamine; sodium nitrite; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; water; acetic acid; dimethyl sulfoxide; trifluoroacetic acid;

DOI:10.1021/jm201717y

upstream raw materials:

tert-butyl (6-cyanonaphthalen-2-yl)carbamate

1-(chloromethyl)-3-(2,2,2-trifluoroacetyl)-2,3-dihydro-1H-benzo[e]indole-7-carbonitrile

tert-butyl 7-cyano-1-(iodomethyl)-1H-benzo[e]indole-3(2H)-carboxylate

1-(iodomethyl)-3-(2,2,2-trifluoroacetyl)-2,3-dihydro-1H-benzo[e]indole-7-carbonitrile

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