3-(3-(4-fluorobenzyl)-7-hydroxy-6-oxo-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoic acid

Base Information

Chemical Name:3-(3-(4-fluorobenzyl)-7-hydroxy-6-oxo-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoic acid
CAS No.:1293387-97-9
Molecular Formula:C₂₀H₁₈FN₃O₄
Molecular Weight:383.379
Hs Code.:

Synonyms:

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Chemical Property of 3-(3-(4-fluorobenzyl)-7-hydroxy-6-oxo-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoic acid

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Technology Process of 3-(3-(4-fluorobenzyl)-7-hydroxy-6-oxo-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoic acid

There total 15 articles about 3-(3-(4-fluorobenzyl)-7-hydroxy-6-oxo-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoic acid 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:

: C₂₄H₂₆FN₃O₄

: 1293387-97-9
3-(3-(4-fluorobenzyl)-7-hydroxy-6-oxo-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoic acid

Guidance literature:: C₂₄H₂₆FN₃O₄; With lithium hydroxide; In methanol; water; at 20 - 45 ℃;

With hydrogenchloride; In water; pH=4;
DOI:10.1021/jm200208d

Reference yield:

: 936-12-9
2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

: 1293387-97-9
3-(3-(4-fluorobenzyl)-7-hydroxy-6-oxo-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoic acid

Guidance literature:: Multi-step reaction with 14 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / Inert atmosphere

1.2: 16.75 h / 20 °C / Inert atmosphere

2.1: N-Bromosuccinimide / ethyl acetate / 1.75 h / 20 °C

2.2: 1.5 h / Reflux

3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h

3.2: 17 h / 20 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.5 h / -78 °C / Inert atmosphere

5.1: palladium 10% on activated carbon; hydrogen; triethylamine / methanol / 1 h / 2068.65 Torr / Inert atmosphere

6.1: triethylamine / dichloromethane / 0 °C

7.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-Methyldicyclohexylamine; lithium chloride; tri tert-butylphosphoniumtetrafluoroborate / 1,4-dioxane / 1 h / 70 °C / Inert atmosphere

8.1: toluene-4-sulfonic acid / tetrahydrofuran / 60 h

9.1: sodium cyanoborohydride; acetic acid / 2 h / 20 °C

10.1: N-iodo-succinimide / N,N-dimethyl-formamide / 1 h / 20 °C

11.1: palladium diacetate; triethylamine; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere

12.1: hydrogen; palladium(II) hydroxide / methanol / 2 h / 760.05 Torr

13.1: sulfuric acid; isopropyl alcohol / 27 h / 40 °C / Reflux

13.2: pH 10

14.1: lithium hydroxide / methanol; water / 20 - 45 °C

14.2: pH 4

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-Bromosuccinimide; N-iodo-succinimide; sulfuric acid; N-Methyldicyclohexylamine; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; palladium diacetate; palladium(II) hydroxide; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; triethylamine; isopropyl alcohol; tris-(o-tolyl)phosphine; lithium chloride; lithium hydroxide; lithium hexamethyldisilazane; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 11.1: Heck reaction;
DOI:10.1021/jm200208d

Reference yield:

: 1293387-95-7
(E)-tert-butyl 3-(3-(4-fluorobenzyl)-6-oxo-7-((2-(trimethylsilyl)ethoxy)methoxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)acrylate

: 1293387-97-9
3-(3-(4-fluorobenzyl)-7-hydroxy-6-oxo-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-1-yl)propanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: hydrogen; palladium(II) hydroxide / methanol / 2 h / 760.05 Torr

2.1: sulfuric acid; isopropyl alcohol / 27 h / 40 °C / Reflux

2.2: pH 10

3.1: lithium hydroxide / methanol; water / 20 - 45 °C

3.2: pH 4

With sulfuric acid; hydrogen; palladium(II) hydroxide; isopropyl alcohol; lithium hydroxide; In methanol; water;
DOI:10.1021/jm200208d