methyl-2-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-4-fluorobenzo[d]thiazole-6-carboxylate

Base Information

• Chemical Name: methyl-2-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-4-fluorobenzo[d]thiazole-6-carboxylate
• CAS No.: 1383816-28-1
• Molecular Formula: C₃₀H₂₇F₄N₃O₅S
• Molecular Weight: 617.621
• Mol file: 1383816-28-1.mol

Synonyms:methyl-2-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-4-fluorobenzo[d]thiazole-6-carboxylate

Chemical Property of methyl-2-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-4-fluorobenzo[d]thiazole-6-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-2-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-4-fluorobenzo[d]thiazole-6-carboxylate

There total 13 articles about methyl-2-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-4-fluorobenzo[d]thiazole-6-carboxylate 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: 75.0%

methyl 2-bromo-4-fluoro-1,3-benzothiazole-6-carboxylate (924287-65-0) + (1R,3S,5S)-3-({5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl}methoxy)-8-azabicyclo[3.2.1]octane (1383822-31-8) → methyl-2-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-4-fluorobenzo[d]thiazole-6-carboxylate (1383816-28-1)

Guidance literature:

With caesium carbonate; In N,N-dimethyl acetamide; at 60 ℃; for 1h;

DOI:10.1021/acs.jmedchem.7b00907

Reference yield:

methyl 3-fluoro-4-nitrobenzoate (185629-31-6) → methyl-2-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-4-fluorobenzo[d]thiazole-6-carboxylate (1383816-28-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogen / palladium 10% on activated carbon / methanol; ethyl acetate / 16 h / 30 °C / Inert atmosphere

2.1: bromine; acetic acid / 49 h / 0 - 30 °C

2.2: pH 8 - 9

3.1: tert.-butylnitrite; copper(ll) bromide / acetonitrile / 48 h / 0 - 30 °C

4.1: caesium carbonate / ISOPROPYLAMIDE / 1 h / 60 °C

With tert.-butylnitrite; hydrogen; bromine; caesium carbonate; acetic acid; copper(ll) bromide; palladium 10% on activated carbon; In methanol; ISOPROPYLAMIDE; ethyl acetate; acetonitrile;

Reference yield:

3-fluoro-4-nitrobenzoic acid (403-21-4) → methyl-2-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-4-fluorobenzo[d]thiazole-6-carboxylate (1383816-28-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogenchloride / water / 16 h / Reflux

2.1: hydrogen / palladium 10% on activated carbon / methanol; ethyl acetate / 16 h / 30 °C / Inert atmosphere

3.1: bromine; acetic acid / 49 h / 0 - 30 °C

3.2: pH 8 - 9

4.1: tert.-butylnitrite; copper(ll) bromide / acetonitrile / 48 h / 0 - 30 °C

5.1: caesium carbonate / ISOPROPYLAMIDE / 1 h / 60 °C

With hydrogenchloride; tert.-butylnitrite; hydrogen; bromine; caesium carbonate; acetic acid; copper(ll) bromide; palladium 10% on activated carbon; In methanol; ISOPROPYLAMIDE; water; ethyl acetate; acetonitrile;

upstream raw materials:

2-(trifluoromethoxy)benzaldehyde

methyl 3-fluoro-4-nitrobenzoate

methyl 4-amino-3-fluorobenzene carboxylate

methyl 2-amino-4-fluoro-1,3-benzothiazole-6-carboxylate

Downstream raw materials:

2-[(1R,3r,5S)-3-({5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl}methoxy)-8-azabicyclo[3.2.1]octan-8-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid