dimethylamino-acetic acid 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-ylmethyl-ester

Base Information

• Chemical Name: dimethylamino-acetic acid 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-ylmethyl-ester
• CAS No.: 1312016-69-5
• Molecular Formula: C₂₆H₃₃N₃O₄S
• Molecular Weight: 483.632

Synonyms:dimethylamino-acetic acid 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-ylmethyl-ester

Chemical Property of dimethylamino-acetic acid 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-ylmethyl-ester

Chemical Property:

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Technology Process of dimethylamino-acetic acid 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-ylmethyl-ester

There total 20 articles about dimethylamino-acetic acid 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-ylmethyl-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: 54.9%

dimethylaminoacetic acid (1118-68-9) + {2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-methanol (1312016-04-8) → dimethylamino-acetic acid 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-ylmethyl-ester (1312016-69-5)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25 ℃; for 6h;

Reference yield:

7-Azaindole (271-63-6) → dimethylamino-acetic acid 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-ylmethyl-ester (1312016-69-5)

Guidance literature:

Multi-step reaction with 18 steps

1.1: triethylamine; formic acid / palladium 10% on activated carbon / 120 h / 0 - 80 °C

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

2.2: 3 h / 0 °C

3.1: bromine; pyridine / dichloromethane / 2 h / 0 °C

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h

5.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.08 h / 0 °C

5.2: 12.25 h / 0 - 25 °C

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 15 h / 85 °C

7.1: 1,4-bis(9-O-dihydroquinidine)phthalazine; water; methanesulfonamide / tert-butyl alcohol / 12 h / 0 °C

7.2: 0.5 h / 25 °C

8.1: toluene-4-sulfonic acid / dichloromethane / 12 h / 25 °C

9.1: lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 °C

9.2: 1 h / -78 °C

10.1: Dess-Martin periodane / dichloromethane / 1 h / 25 °C

11.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C

11.2: 1.5 h / -78 °C

12.1: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 1.5 h / 100 °C / Microwave irradiation

13.1: sodium hydroxide; water / ethanol / 1 h / 100 °C

13.2: pH 4 - 5

14.1: hydrogen / palladium 10% on activated carbon / methanol / 12 h / 50 °C / 37503.8 Torr

15.1: hydrogenchloride; water / tetrahydrofuran / 1 h / Reflux

16.1: sodium periodate / water; tetrahydrofuran / 2 h / 0 - 20 °C

17.1: sodium tetrahydroborate; methanol / 2 h / 0 - 20 °C

18.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / N,N-dimethyl-formamide / 6 h / 25 °C

With 4-methyl-morpholine; pyridine; hydrogenchloride; methanol; sodium tetrahydroborate; sodium periodate; formic acid; methanesulfonamide; tetrabutylammomium bromide; water; hydrogen; bromine; sodium hydride; sodium carbonate; benzotriazol-1-ol; Dess-Martin periodane; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; lithium hexamethyldisilazane; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol;

Reference yield:

2-cyclopentyl-ethanol (766-00-7) → dimethylamino-acetic acid 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-ylmethyl-ester (1312016-69-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: pyridinium chlorochromate / dichloromethane / 3 h / 25 °C

2.1: lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 °C

2.2: 1 h / -78 °C

3.1: Dess-Martin periodane / dichloromethane / 1 h / 25 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C

4.2: 1.5 h / -78 °C

5.1: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 1.5 h / 100 °C / Microwave irradiation

6.1: sodium hydroxide; water / ethanol / 1 h / 100 °C

6.2: pH 4 - 5

7.1: hydrogen / palladium 10% on activated carbon / methanol / 12 h / 50 °C / 37503.8 Torr

8.1: hydrogenchloride; water / tetrahydrofuran / 1 h / Reflux

9.1: sodium periodate / water; tetrahydrofuran / 2 h / 0 - 20 °C

10.1: sodium tetrahydroborate; methanol / 2 h / 0 - 20 °C

11.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / N,N-dimethyl-formamide / 6 h / 25 °C

With 4-methyl-morpholine; hydrogenchloride; methanol; sodium tetrahydroborate; sodium periodate; water; hydrogen; sodium carbonate; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridinium chlorochromate; sodium hydroxide; lithium hexamethyldisilazane; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

7-Azaindole

2-cyclopentyl-ethanol

dimethylaminoacetic acid

{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-methanol

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