3-amino-6-bromo-N-(4-((1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-4,5-dimethylcyclohexyl)pyridin-3-yl)picolinamide

Base Information

• Chemical Name: 3-amino-6-bromo-N-(4-((1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-4,5-dimethylcyclohexyl)pyridin-3-yl)picolinamide
• CAS No.: 1395284-95-3
• Molecular Formula: C₂₅H₃₇BrN₄O₃Si
• Molecular Weight: 549.583

Synonyms:3-amino-6-bromo-N-(4-((1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-4,5-dimethylcyclohexyl)pyridin-3-yl)picolinamide

Chemical Property of 3-amino-6-bromo-N-(4-((1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-4,5-dimethylcyclohexyl)pyridin-3-yl)picolinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-amino-6-bromo-N-(4-((1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-4,5-dimethylcyclohexyl)pyridin-3-yl)picolinamide

There total 17 articles about 3-amino-6-bromo-N-(4-((1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-4,5-dimethylcyclohexyl)pyridin-3-yl)picolinamide 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-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enone (1187055-95-3) → 3-amino-6-bromo-N-(4-((1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-4,5-dimethylcyclohexyl)pyridin-3-yl)picolinamide (1395284-95-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / 0 - 20 °C

2.1: dichloromethane / 19 h / 0 - 20 °C

3.1: tetrahydrofuran / 18 h / 0 - 20 °C

4.1: sodium hydrogencarbonate / water / 5 h / 20 °C

5.1: cerium(III) chloride heptahydrate / methanol / 1 h / 20 °C

5.2: 0.5 h / 0 °C

6.1: N-Bromosuccinimide / tetrahydrofuran; water / 3 h / 0 °C

7.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C

8.1: hydrogen; 10 wt% Pd(OH)2 on carbon / methanol / 96 h / 20 °C / 10343.2 Torr

9.1: AD column / n-heptane; isopropyl alcohol / Resolution of racemate

10.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 16 h

With 1H-imidazole; N-Bromosuccinimide; 1-hydroxy-7-aza-benzotriazole; cerium(III) chloride heptahydrate; 10 wt% Pd(OH)2 on carbon; hydrogen; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; n-heptane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/acs.jmedchem.0c01279

Reference yield:

(±)-4-(5-methyl-3-(trimethylsilyloxy)cyclohexa-1,3-dienyl)-3-nitropyridine (1395280-10-0) → 3-amino-6-bromo-N-(4-((1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-4,5-dimethylcyclohexyl)pyridin-3-yl)picolinamide (1395284-95-3)

Guidance literature:

Multi-step reaction with 16 steps

1.1: oxone / ethyl acetate; water; acetone / 3.5 h / 0 - 20 °C

2.1: pyridine / 20 °C

3.1: cerium(III) chloride heptahydrate / methanol; tetrahydrofuran / 2 h / 20 °C

3.2: 0 - 20 °C

4.1: 1H-imidazole / dichloromethane / 20 °C

5.1: hydrogen; palladium on activated charcoal / ethanol; ethyl acetate / 20 °C

6.1: dmap / dichloromethane / 20 °C

7.1: lithium hydroxide / tetrahydrofuran / 60 °C

7.2: 20 °C

8.1: tetrahydrofuran / 35 °C

9.1: hydrogenchloride / water; acetone

10.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 20 °C

11.1: pyridine / dichloromethane / 0 °C

12.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C

13.1: 1H-imidazole / dichloromethane / 20 °C

14.1: trifluoroacetic acid / dichloromethane / 1.5 h

15.1: AD column / n-heptane; isopropyl alcohol / Resolution of racemate

16.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 16 h

With pyridine; 1H-imidazole; hydrogenchloride; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; 1-hydroxy-7-aza-benzotriazole; oxone; cerium(III) chloride heptahydrate; palladium on activated charcoal; hydrogen; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; acetone; 7.2: |Dess-Martin Oxidation;

DOI:10.1021/acs.jmedchem.0c01279

Reference yield:

cis-(±)-(1S,6S)-6-methyl-4-(3-nitropyridin-4-yl)-2-oxocyclohex-3-enyl acetate → 3-amino-6-bromo-N-(4-((1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-4,5-dimethylcyclohexyl)pyridin-3-yl)picolinamide (1395284-95-3)

Guidance literature:

Multi-step reaction with 14 steps

1.1: cerium(III) chloride heptahydrate / methanol; tetrahydrofuran / 2 h / 20 °C

1.2: 0 - 20 °C

2.1: 1H-imidazole / dichloromethane / 20 °C

3.1: hydrogen; palladium on activated charcoal / ethanol; ethyl acetate / 20 °C

4.1: dmap / dichloromethane / 20 °C

5.1: lithium hydroxide / tetrahydrofuran / 60 °C

5.2: 20 °C

6.1: tetrahydrofuran / 35 °C

7.1: hydrogenchloride / water; acetone

8.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 20 °C

9.1: pyridine / dichloromethane / 0 °C

10.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C

11.1: 1H-imidazole / dichloromethane / 20 °C

12.1: trifluoroacetic acid / dichloromethane / 1.5 h

13.1: AD column / n-heptane; isopropyl alcohol / Resolution of racemate

14.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 16 h

With pyridine; 1H-imidazole; hydrogenchloride; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; 1-hydroxy-7-aza-benzotriazole; cerium(III) chloride heptahydrate; palladium on activated charcoal; hydrogen; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; acetone; 5.2: |Dess-Martin Oxidation;

DOI:10.1021/acs.jmedchem.0c01279

upstream raw materials:

3-amino-6-bromopyridine-2-carboxylic acid

(1R,2R,4R,6S)-4-(3-aminopyridin-4-yl)-2-((tert-butyldimethylsilyl)oxy)-1,6-dimethylcyclohexanol

(±)-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enone

(±)-4-(5-methyl-3-(trimethylsilyloxy)cyclohexa-1,3-dienyl)-3-nitropyridine

Downstream raw materials:

5-amino-N-(4-((1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-4,5-dimethylcyclohexyl)pyridin-3-yl)-3'-fluoro-2,2'-bipyridine-6-carboxamide

3-amino-N-(4-((1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-4,5-dimethylcyclohexyl)pyridin-3-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide

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