9H-fluoren-9-ylmethyl N-[(5S)-5-[[6-[[3-[4-(2-carbamoylphenoxy)phenyl]-2,5-dioxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carbonyl]amino]-5-cyano-pentyl]carbamate

Base Information

• Chemical Name: 9H-fluoren-9-ylmethyl N-[(5S)-5-[[6-[[3-[4-(2-carbamoylphenoxy)phenyl]-2,5-dioxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carbonyl]amino]-5-cyano-pentyl]carbamate
• CAS No.: 1596360-80-3
• Molecular Formula: C₄₆H₄₁N₉O₇
• Molecular Weight: 831.888

Synonyms:9H-fluoren-9-ylmethyl N-[(5S)-5-[[6-[[3-[4-(2-carbamoylphenoxy)phenyl]-2,5-dioxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carbonyl]amino]-5-cyano-pentyl]carbamate

Chemical Property of 9H-fluoren-9-ylmethyl N-[(5S)-5-[[6-[[3-[4-(2-carbamoylphenoxy)phenyl]-2,5-dioxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carbonyl]amino]-5-cyano-pentyl]carbamate

Chemical Property:

Purity/Quality:

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Technology Process of 9H-fluoren-9-ylmethyl N-[(5S)-5-[[6-[[3-[4-(2-carbamoylphenoxy)phenyl]-2,5-dioxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carbonyl]amino]-5-cyano-pentyl]carbamate

There total 18 articles about 9H-fluoren-9-ylmethyl N-[(5S)-5-[[6-[[3-[4-(2-carbamoylphenoxy)phenyl]-2,5-dioxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carbonyl]amino]-5-cyano-pentyl]carbamate 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:

5-bromo-4-methylamino-pyrimidine-2-carbonitrile (1596360-12-1) → 9H-fluoren-9-ylmethyl N-[(5S)-5-[[6-[[3-[4-(2-carbamoylphenoxy)phenyl]-2,5-dioxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carbonyl]amino]-5-cyano-pentyl]carbamate (1596360-80-3)

Guidance literature:

Multi-step reaction with 9 steps

1: hydrogenchloride / 15 h / 20 °C

2: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 4 h / 80 °C

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 2 h / 20 - 100 °C

4: hydrogenchloride; sodium hydrogencarbonate / methanol / 3 h / 20 °C

5: carbon tetrabromide; triphenylphosphine / dichloromethane / 3.5 h / 0 - 20 °C

6: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C

7: water; lithium hydroxide monohydrate / methanol; tetrahydrofuran / 3 h / 20 °C

8: N,N-dimethyl-formamide / 15 h / 20 °C

9: triethylamine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 15 h / 0 - 20 °C

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1-hydroxy-7-aza-benzotriazole; lithium hydroxide monohydrate; carbon tetrabromide; water; sodium hydrogencarbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2014.02.002

Reference yield:

methyl 5-bromo-4-methylamino-pyrimidine-2-carboxylate (1523354-68-8) → 9H-fluoren-9-ylmethyl N-[(5S)-5-[[6-[[3-[4-(2-carbamoylphenoxy)phenyl]-2,5-dioxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carbonyl]amino]-5-cyano-pentyl]carbamate (1596360-80-3)

Guidance literature:

Multi-step reaction with 8 steps

1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 4 h / 80 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 2 h / 20 - 100 °C

3: hydrogenchloride; sodium hydrogencarbonate / methanol / 3 h / 20 °C

4: carbon tetrabromide; triphenylphosphine / dichloromethane / 3.5 h / 0 - 20 °C

5: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C

6: water; lithium hydroxide monohydrate / methanol; tetrahydrofuran / 3 h / 20 °C

7: N,N-dimethyl-formamide / 15 h / 20 °C

8: triethylamine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 15 h / 0 - 20 °C

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1-hydroxy-7-aza-benzotriazole; lithium hydroxide monohydrate; carbon tetrabromide; water; sodium hydrogencarbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2014.02.002

Reference yield:

methyl2-(4-nitrophenoxy)benzoate (212189-50-9) → 9H-fluoren-9-ylmethyl N-[(5S)-5-[[6-[[3-[4-(2-carbamoylphenoxy)phenyl]-2,5-dioxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carbonyl]amino]-5-cyano-pentyl]carbamate (1596360-80-3)

Guidance literature:

Multi-step reaction with 11 steps

1: hydrogen / methanol / 3 h / 20 °C

2: dmap / tetrahydrofuran / 16 h / 20 °C

3: lithium hydroxide monohydrate / methanol / 60 °C

4: triethylamine; benzotriazol-1-ol; ammonium chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C

5: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C

6: potassium carbonate / N,N-dimethyl-formamide / 17 h / 20 °C

7: acetic acid / 13 h / 20 - 110 °C

8: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C

9: water; lithium hydroxide monohydrate / methanol; tetrahydrofuran / 3 h / 20 °C

10: N,N-dimethyl-formamide / 15 h / 20 °C

11: triethylamine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 15 h / 0 - 20 °C

With dmap; 1-hydroxy-7-aza-benzotriazole; lithium hydroxide monohydrate; water; hydrogen; potassium carbonate; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2014.02.002

upstream raw materials:

5-bromo-4-methylamino-pyrimidine-2-carbonitrile

methyl 5-bromo-4-methylamino-pyrimidine-2-carboxylate

methyl2-(4-nitrophenoxy)benzoate

methyl2-(4-aminophenoxy)benzoate

Downstream raw materials:

N-[(1S)-5-amino-1-cyano-pentyl]-6-[[3-[4-(2-carbamoylphenoxy)phenyl]-2,5-dioxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carboxamide

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