[6-chloro-4-cyclopropylethynyl-1-(4-methoxy-benzyl)-2-oxo-4-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-3-yl]-carbamic acid methyl ester

Base Information

Chemical Name:[6-chloro-4-cyclopropylethynyl-1-(4-methoxy-benzyl)-2-oxo-4-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-3-yl]-carbamic acid methyl ester
CAS No.:364360-74-7
Molecular Formula:C₂₅H₂₂ClF₃N₂O₄
Molecular Weight:506.909
Hs Code.:

Synonyms:[6-chloro-4-cyclopropylethynyl-1-(4-methoxy-benzyl)-2-oxo-4-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-3-yl]-carbamic acid methyl ester

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Chemical Property of [6-chloro-4-cyclopropylethynyl-1-(4-methoxy-benzyl)-2-oxo-4-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-3-yl]-carbamic acid methyl ester

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Technology Process of [6-chloro-4-cyclopropylethynyl-1-(4-methoxy-benzyl)-2-oxo-4-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-3-yl]-carbamic acid methyl ester

There total 10 articles about [6-chloro-4-cyclopropylethynyl-1-(4-methoxy-benzyl)-2-oxo-4-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-3-yl]-carbamic acid methyl 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: 67.0%

: 79-22-1
methyl chloroformate

: 364360-76-9
3-amino-6-chloro-4-cyclopropylethynyl-1-(4-methoxy-benzyl)-4-trifluoromethyl-3,4-dihydro-1H-quinolin-2-one

: 364360-74-7
[6-chloro-4-cyclopropylethynyl-1-(4-methoxy-benzyl)-2-oxo-4-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-3-yl]-carbamic acid methyl ester

Guidance literature:: With potassium carbonate; In tetrahydrofuran; at 25 ℃; for 2h;
DOI:10.1016/S0960-894X(01)00331-6

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 364360-74-7
[6-chloro-4-cyclopropylethynyl-1-(4-methoxy-benzyl)-2-oxo-4-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-3-yl]-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 74 percent / K₂CO₃ / dimethylformamide / 14 h / 25 °C

2: 93 percent / LDA; tosyl azide / tetrahydrofuran / 1 h / 0 - 25 °C

3: 83 percent / SnCl₂*H₂O / methanol; tetrahydrofuran / 3 h / 25 °C

4: 67 percent / K₂CO₃ / tetrahydrofuran / 2 h / 25 °C

With 4-toluenesulfonyl azide; potassium carbonate; tin(ll) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(01)00331-6

Reference yield:

: 154598-53-5
1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone

: 364360-74-7
[6-chloro-4-cyclopropylethynyl-1-(4-methoxy-benzyl)-2-oxo-4-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-3-yl]-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: K₂CO₃ / tetrahydrofuran / 3 h / 25 °C

2: 89 percent / dimethylformamide / 18 h / 25 °C

3: 94 percent / Ac₂O; DMAP / CH₂Cl₂ / 18 h / 25 °C

4: 75 percent / n-BuLi / tetrahydrofuran / -78 - 25 °C

5: 77 percent / Al/Hg / ethanol / 1 h / Heating

6: 74 percent / K₂CO₃ / dimethylformamide / 14 h / 25 °C

7: 93 percent / LDA; tosyl azide / tetrahydrofuran / 1 h / 0 - 25 °C

8: 83 percent / SnCl₂*H₂O / methanol; tetrahydrofuran / 3 h / 25 °C

9: 67 percent / K₂CO₃ / tetrahydrofuran / 2 h / 25 °C

With dmap; aluminum amalgam; n-butyllithium; 4-toluenesulfonyl azide; acetic anhydride; potassium carbonate; tin(ll) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(01)00331-6