8-[ethyl-(1-ethyl-pyrrolidin-3-yl)-amino]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

Base Information

Chemical Name:8-[ethyl-(1-ethyl-pyrrolidin-3-yl)-amino]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide
CAS No.:919794-72-2
Molecular Formula:C₃₅H₅₁N₅O₅Si
Molecular Weight:649.906
Hs Code.:

8-[ethyl-(1-ethyl-pyrrolidin-3-yl)-amino]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

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Chemical Property of 8-[ethyl-(1-ethyl-pyrrolidin-3-yl)-amino]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

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Technology Process of 8-[ethyl-(1-ethyl-pyrrolidin-3-yl)-amino]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

There total 6 articles about 8-[ethyl-(1-ethyl-pyrrolidin-3-yl)-amino]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide 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:

: 442549-54-4
8-bromo-6-methoxy-4-oxo-1,4-dihydro-quinoline-2-carboxylic acid

: 919794-72-2
8-[ethyl-(1-ethyl-pyrrolidin-3-yl)-amino]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

Guidance literature:: Multi-step reaction with 3 steps

1: 58 percent / 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium BF₄; 1-hydroxybenzotriazole; ethyldiisopropylamine / dimethylformamide / 16 h / 20 °C

2: 80 percent / NaH / 1-methyl-pyrrolidin-2-one / 4.5 h / 20 °C

3: molecular sieves 4 Angstroem; rac-BINAP; Cs₂CO₃ / Pd₂(dba)3 / toluene / 17 h / Heating

With 4 A molecular sieve; sodium hydride; benzotriazol-1-ol; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide; toluene; 3: Buchwald-Hartwig coupling;
DOI:10.1016/j.bmc.2006.10.037

Reference yield:

: 442549-50-0
8-bromo-6-methoxy-4-oxo-1,4-dihydroquinoline-2-carboxylic acid methyl ester

: 919794-72-2
8-[ethyl-(1-ethyl-pyrrolidin-3-yl)-amino]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / lithium hydroxide monohydrate / tetrahydrofuran; methanol; H₂O / 5 h / 20 °C

2: 58 percent / 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium BF₄; 1-hydroxybenzotriazole; ethyldiisopropylamine / dimethylformamide / 16 h / 20 °C

3: 80 percent / NaH / 1-methyl-pyrrolidin-2-one / 4.5 h / 20 °C

4: molecular sieves 4 Angstroem; rac-BINAP; Cs₂CO₃ / Pd₂(dba)3 / toluene / 17 h / Heating

With lithium hydroxide; 4 A molecular sieve; sodium hydride; benzotriazol-1-ol; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; water; N,N-dimethyl-formamide; toluene; 4: Buchwald-Hartwig coupling;
DOI:10.1016/j.bmc.2006.10.037

Reference yield:

: 442549-49-7
2-(2-bromo-4-methoxyphenylamino)but-2-enedioic acid dimethyl ester

: 919794-72-2
8-[ethyl-(1-ethyl-pyrrolidin-3-yl)-amino]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / diphenyl ether; various solvent(s) / 0.75 h / 240 - 245 °C

2: 97 percent / lithium hydroxide monohydrate / tetrahydrofuran; methanol; H₂O / 5 h / 20 °C

3: 58 percent / 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium BF₄; 1-hydroxybenzotriazole; ethyldiisopropylamine / dimethylformamide / 16 h / 20 °C

4: 80 percent / NaH / 1-methyl-pyrrolidin-2-one / 4.5 h / 20 °C

5: molecular sieves 4 Angstroem; rac-BINAP; Cs₂CO₃ / Pd₂(dba)3 / toluene / 17 h / Heating

With lithium hydroxide; 4 A molecular sieve; sodium hydride; benzotriazol-1-ol; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; diphenylether; water; N,N-dimethyl-formamide; toluene; 5: Buchwald-Hartwig coupling;
DOI:10.1016/j.bmc.2006.10.037