3-[6-amino-4-(tert-butoxycarbonyl-methyl-amino)-1-methyl-1H-imidazo[4,5-d]pyridin-7-ylethynyl]-benzoic acid tert-butyl ester

Base Information

• Chemical Name: 3-[6-amino-4-(tert-butoxycarbonyl-methyl-amino)-1-methyl-1H-imidazo[4,5-d]pyridin-7-ylethynyl]-benzoic acid tert-butyl ester
• CAS No.: 914943-90-1
• Molecular Formula: C₂₆H₃₁N₅O₄
• Molecular Weight: 477.563
• Mol file: 914943-90-1.mol

Synonyms:3-[6-amino-4-(tert-butoxycarbonyl-methyl-amino)-1-methyl-1H-imidazo[4,5-d]pyridin-7-ylethynyl]-benzoic acid tert-butyl ester

Chemical Property of 3-[6-amino-4-(tert-butoxycarbonyl-methyl-amino)-1-methyl-1H-imidazo[4,5-d]pyridin-7-ylethynyl]-benzoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[6-amino-4-(tert-butoxycarbonyl-methyl-amino)-1-methyl-1H-imidazo[4,5-d]pyridin-7-ylethynyl]-benzoic acid tert-butyl ester

There total 16 articles about 3-[6-amino-4-(tert-butoxycarbonyl-methyl-amino)-1-methyl-1H-imidazo[4,5-d]pyridin-7-ylethynyl]-benzoic acid tert-butyl 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: 65.0%

tert-butyl 3-ethynylbenzoate (914943-91-2) + tert-butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate (914942-88-4) → 3-[6-amino-4-(tert-butoxycarbonyl-methyl-amino)-1-methyl-1H-imidazo[4,5-d]pyridin-7-ylethynyl]-benzoic acid tert-butyl ester (914943-90-1)

Guidance literature:

With triethylamine; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 20 - 90 ℃; for 0.833333h;

Reference yield:

2,4,6-trichloropyridine (16063-69-7) → 3-[6-amino-4-(tert-butoxycarbonyl-methyl-amino)-1-methyl-1H-imidazo[4,5-d]pyridin-7-ylethynyl]-benzoic acid tert-butyl ester (914943-90-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: ethanol / 1.66 - 24 h / 20 - 60 °C

2.1: sulfuric acid; nitric acid / 0.92 h / 0 - 6 °C

3.1: ammonium chloride / iron / water / 2 h / 20 - 90 °C

4.1: ethanol / 15 h / 20 - 80 °C

5.1: ethanol / 3 - 24 h / 82 - 120 °C

6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.58 - 1 h / -78 - -20 °C

6.2: 3.5 - 16 h / -20 - 20 °C

7.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / N,N-dimethyl acetamide / 5 - 8.33 h / 110 - 115 °C

8.1: hydrogenchloride / tetrahydrofuran; water / 0.33 - 0.5 h / 0 - 5 °C

8.2: pH 12

9.1: N-iodo-succinimide / acetonitrile / 2.25 h / 0 °C / Cooling with ethanol-dry ice

10.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.83 h / 20 - 90 °C

With hydrogenchloride; N-iodo-succinimide; sulfuric acid; nitric acid; sodium hexamethyldisilazane; ammonium chloride; caesium carbonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; iron; In tetrahydrofuran; ethanol; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

pyridin-4-ol (626-64-2,157061-69-3) → 3-[6-amino-4-(tert-butoxycarbonyl-methyl-amino)-1-methyl-1H-imidazo[4,5-d]pyridin-7-ylethynyl]-benzoic acid tert-butyl ester (914943-90-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: sulfuric acid; nitric acid / 12 h / 140 °C

2.1: phosphorus pentachloride; trichlorophosphate / 12 h

3.1: tetrahydrofuran / 1.33 h / 0 - 20 °C

4.1: hydrogenchloride; tin(ll) chloride / 3 h / 90 °C

4.2: 0 °C

5.1: acetonitrile / 4 h / Heating / reflux

6.1: hypophosphorous acid; sodium nitrite / water / 0.75 h / 0 - 20 °C

7.1: ethanol / 3 - 24 h / 82 - 120 °C

8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.58 - 1 h / -78 - -20 °C

8.2: 3.5 - 16 h / -20 - 20 °C

9.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / N,N-dimethyl acetamide / 5 - 8.33 h / 110 - 115 °C

10.1: hydrogenchloride / tetrahydrofuran; water / 0.33 - 0.5 h / 0 - 5 °C

10.2: pH 12

11.1: N-iodo-succinimide / acetonitrile / 2.25 h / 0 °C / Cooling with ethanol-dry ice

12.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.83 h / 20 - 90 °C

With hydrogenchloride; N-iodo-succinimide; phosphorus pentachloride; sulfuric acid; nitric acid; hypophosphorous acid; sodium hexamethyldisilazane; caesium carbonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tin(ll) chloride; sodium nitrite; trichlorophosphate; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; ethanol; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

tert-butyl 3-ethynylbenzoate

tert-butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate

pyridin-4-ol

2,4,6-trichloropyridine

Refernces