2-[(1R,2S,3R,5S,6R)-3,5-Diazido-2-hydroxy-6-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-N-(3-dimethylamino-propyl)-acetamide

Base Information

Chemical Name:2-[(1R,2S,3R,5S,6R)-3,5-Diazido-2-hydroxy-6-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-N-(3-dimethylamino-propyl)-acetamide
CAS No.:870180-79-3
Molecular Formula:C₂₄H₃₀F₃N₉O₄S
Molecular Weight:597.621
Hs Code.:

2-[(1R,2S,3R,5S,6R)-3,5-Diazido-2-hydroxy-6-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-N-(3-dimethylamino-propyl)-acetamide

Synonyms:2-[(1R,2S,3R,5S,6R)-3,5-Diazido-2-hydroxy-6-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-N-(3-dimethylamino-propyl)-acetamide

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Chemical Property of 2-[(1R,2S,3R,5S,6R)-3,5-Diazido-2-hydroxy-6-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-N-(3-dimethylamino-propyl)-acetamide

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Technology Process of 2-[(1R,2S,3R,5S,6R)-3,5-Diazido-2-hydroxy-6-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-N-(3-dimethylamino-propyl)-acetamide

There total 7 articles about 2-[(1R,2S,3R,5S,6R)-3,5-Diazido-2-hydroxy-6-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-N-(3-dimethylamino-propyl)-acetamide 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: 81.0%

: 870180-47-5
[(1R,2S,3R,5S,6R)-3,5-Diazido-2-hydroxy-6-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-acetic acid

: 109-55-7
1-amino-3-(dimethylamino)propane

: 870180-79-3
2-[(1R,2S,3R,5S,6R)-3,5-Diazido-2-hydroxy-6-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-N-(3-dimethylamino-propyl)-acetamide

Guidance literature:: [(1R,2S,3R,5S,6R)-3,5-Diazido-2-hydroxy-6-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-acetic acid; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20 ℃; for 0.166667h;

1-amino-3-(dimethylamino)propane; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/j.bmcl.2005.08.027

Reference yield:

: 64415-07-2
4-mercapto 7-trifluoromethyl quinoline

: 870180-79-3
2-[(1R,2S,3R,5S,6R)-3,5-Diazido-2-hydroxy-6-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-N-(3-dimethylamino-propyl)-acetamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / acetonitrile / 0.25 h / 20 °C

1.2: 1.15 g / acetonitrile / 2.5 h / 20 °C

2.1: 91 percent / aq. NH₃ / methanol / 16 h / 20 °C

3.1: NaH / tetrahydrofuran / 1 h / 0 - 20 °C

3.2: 25 percent / tetrahydrofuran / 16 h / 20 °C

4.1: HATU; diisopropylethylamine / CH₂Cl₂ / 0.17 h / 20 °C

4.2: 81 percent / CH₂Cl₂ / 2 h / 20 °C

With ammonium hydroxide; sodium hydride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1016/j.bmcl.2005.08.027

Reference yield:

: 236115-61-0
[(1S,2S,3R,4S,6R)-2-acetoxy-4,6-diazido-3-hydroxy-cyclohexyl] acetate

: 870180-79-3
2-[(1R,2S,3R,5S,6R)-3,5-Diazido-2-hydroxy-6-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexyloxy]-N-(3-dimethylamino-propyl)-acetamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: 80 percent / AcOH; Ac₂O / 60 h / 20 °C

2.1: SO₂Cl₂ / CH₂Cl₂ / 0.5 h / 20 °C

3.1: NaH / acetonitrile / 0.25 h / 20 °C

3.2: 1.15 g / acetonitrile / 2.5 h / 20 °C

4.1: 91 percent / aq. NH₃ / methanol / 16 h / 20 °C

5.1: NaH / tetrahydrofuran / 1 h / 0 - 20 °C

5.2: 25 percent / tetrahydrofuran / 16 h / 20 °C

6.1: HATU; diisopropylethylamine / CH₂Cl₂ / 0.17 h / 20 °C

6.2: 81 percent / CH₂Cl₂ / 2 h / 20 °C

With ammonium hydroxide; sulfuryl dichloride; acetic anhydride; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1.1: Pummerer rearrangement;
DOI:10.1016/j.bmcl.2005.08.027