7-((1R,4R,6S)-5-Benzyl-6-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-1-tert-butyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

Base Information

• Chemical Name: 7-((1R,4R,6S)-5-Benzyl-6-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-1-tert-butyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
• CAS No.: 142928-75-4
• Molecular Formula: C₂₉H₃₅FN₄O₃
• Molecular Weight: 506.62

Synonyms:7-((1R,4R,6S)-5-Benzyl-6-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-1-tert-butyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

Chemical Property of 7-((1R,4R,6S)-5-Benzyl-6-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-1-tert-butyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

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Technology Process of 7-((1R,4R,6S)-5-Benzyl-6-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-1-tert-butyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

There total 4 articles about 7-((1R,4R,6S)-5-Benzyl-6-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-1-tert-butyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl 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: 62.5%

7-chloro-6-fluoro-5-methyl-1-(1,1-dimethylethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid ethyl ester (138668-30-1) + (1R,4R,6S)-6-methyl-5-(phenylmethyl)2,5-diazabicyclo<2.2.1>heptane dihydrobromide (141871-22-9,141902-28-5) → 7-((1R,4R,6S)-5-Benzyl-6-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-1-tert-butyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester (142928-75-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile;

DOI:10.1021/jm00093a024

Reference yield:

(2R,4S)-1-(4-tolylsulfonyl)-2-(1-hydroxyethyl)-4-hydroxypyrrolidine (142896-66-0,142896-67-1) → 7-((1R,4R,6S)-5-Benzyl-6-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-1-tert-butyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester (142928-75-4)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 1 h / 5 °C

2: 31 percent / toluene / 88 h / Heating

3: 88.5 percent / 33percent HBr, AcOH / 80 °C

4: 62.5 percent / 1,-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile

With pyridine; hydrogen bromide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; acetonitrile;

DOI:10.1021/jm00093a024

Reference yield:

C27H31NO8S3 (141621-13-8,142896-68-2,142928-72-1) → 7-((1R,4R,6S)-5-Benzyl-6-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-1-tert-butyl-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester (142928-75-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 31 percent / toluene / 88 h / Heating

2: 88.5 percent / 33percent HBr, AcOH / 80 °C

3: 62.5 percent / 1,-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile

With hydrogen bromide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; acetonitrile;

DOI:10.1021/jm00093a024

upstream raw materials:

7-chloro-6-fluoro-5-methyl-1-(1,1-dimethylethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid ethyl ester

(1R,4R,6S)-6-methyl-5-(phenylmethyl)2,5-diazabicyclo<2.2.1>heptane dihydrobromide

(2R,4S)-1-(4-tolylsulfonyl)-2-(1-hydroxyethyl)-4-hydroxypyrrolidine

C₂₇H₃₁NO₈S₃

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