(3-chloro-5-nitro-benzyl)-{6-[2-(5-ethyl-4-methyl-thiazol-2-yl)-ethyl]-4-methylsulfanyl-pyridin-2-yl}-carbamic acid tert-butyl ester

Base Information

Chemical Name:(3-chloro-5-nitro-benzyl)-{6-[2-(5-ethyl-4-methyl-thiazol-2-yl)-ethyl]-4-methylsulfanyl-pyridin-2-yl}-carbamic acid tert-butyl ester
CAS No.:693225-86-4
Molecular Formula:C₂₆H₃₁ClN₄O₄S₂
Molecular Weight:563.142
Hs Code.:

(3-chloro-5-nitro-benzyl)-{6-[2-(5-ethyl-4-methyl-thiazol-2-yl)-ethyl]-4-methylsulfanyl-pyridin-2-yl}-carbamic acid <i>tert</i>-butyl ester

Synonyms:(3-chloro-5-nitro-benzyl)-{6-[2-(5-ethyl-4-methyl-thiazol-2-yl)-ethyl]-4-methylsulfanyl-pyridin-2-yl}-carbamic acid tert-butyl ester

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Chemical Property of (3-chloro-5-nitro-benzyl)-{6-[2-(5-ethyl-4-methyl-thiazol-2-yl)-ethyl]-4-methylsulfanyl-pyridin-2-yl}-carbamic acid tert-butyl ester

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Technology Process of (3-chloro-5-nitro-benzyl)-{6-[2-(5-ethyl-4-methyl-thiazol-2-yl)-ethyl]-4-methylsulfanyl-pyridin-2-yl}-carbamic acid tert-butyl ester

There total 10 articles about (3-chloro-5-nitro-benzyl)-{6-[2-(5-ethyl-4-methyl-thiazol-2-yl)-ethyl]-4-methylsulfanyl-pyridin-2-yl}-carbamic acid tert-butyl 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: 100.0%

: 1-chloro-3-(chloromethyl)-5-nitrobenzene

: 693225-85-3
{6-[2-(5-ethyl-4-methyl-thiazol-2-yl)-ethyl]-4-methylsulfanyl-pyridin-2-yl}-carbamic acid tert-butyl ester

: 693225-86-4
(3-chloro-5-nitro-benzyl)-{6-[2-(5-ethyl-4-methyl-thiazol-2-yl)-ethyl]-4-methylsulfanyl-pyridin-2-yl}-carbamic acid tert-butyl ester

Guidance literature:: {6-[2-(5-ethyl-4-methyl-thiazol-2-yl)-ethyl]-4-methylsulfanyl-pyridin-2-yl}-carbamic acid tert-butyl ester; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

1-chloro-3-(chloromethyl)-5-nitrobenzene; In N,N-dimethyl-formamide; at 0 ℃; for 1h;
DOI:10.1016/j.bmcl.2004.01.049

Reference yield:

: 10168-05-5
4-methylsulfanyl-pyridine-2,6-dicarboxylic acid diethyl ester

: 693225-86-4
(3-chloro-5-nitro-benzyl)-{6-[2-(5-ethyl-4-methyl-thiazol-2-yl)-ethyl]-4-methylsulfanyl-pyridin-2-yl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: NaBH₄; CaCl₂ / ethanol / 3 h / 20 °C

2.1: PPTS / CHCl₃ / 1.5 h / 50 °C

3.1: aq. NaOH / methanol / 1 h / 40 °C

4.1: diphenylphosphoryl azide; Et₃N / dioxane / 1 h / 20 °C

4.2: dioxane / 0.5 h / Heating

5.1: p-TsOH; EtOH / 1 h / 40 °C

6.1: SO₃*Py; Et₃N / dimethylsulfoxide / 0.5 h / 20 °C

7.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

8.1: NaBH₄; NiCl₂ / tetrahydrofuran; methanol / 0.5 h / 20 °C

9.1: aq. NaOH / tetrahydrofuran; methanol / 2 h / 40 °C

10.1: 87 percent / EDCI; HOBt; N-methylmorpholine / dimethylformamide / 15 h / 20 °C

11.1: 79 percent / Lawesson's reagent / toluene / 6 h / Heating

12.1: NaH / dimethylformamide / 0.5 h / 0 °C

12.2: 100 percent / dimethylformamide / 1 h / 0 °C

With Lawessons reagent; 4-methyl-morpholine; sodium hydroxide; sodium tetrahydroborate; pyridine-SO₃ complex; ethanol; diphenylphosphoranyl azide; pyridinium p-toluenesulfonate; sodium hydride; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; calcium chloride; nickel dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 7.1: Horner-Emmons reaction;
DOI:10.1016/j.bmcl.2004.01.049

Reference yield:

: 112776-83-7
diethyl 4-bromo-2,6-pyridinedicarboxylate

: 693225-86-4
(3-chloro-5-nitro-benzyl)-{6-[2-(5-ethyl-4-methyl-thiazol-2-yl)-ethyl]-4-methylsulfanyl-pyridin-2-yl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: dimethylformamide / 0.17 h / 0 °C

2.1: NaBH₄; CaCl₂ / ethanol / 3 h / 20 °C

3.1: PPTS / CHCl₃ / 1.5 h / 50 °C

4.1: aq. NaOH / methanol / 1 h / 40 °C

5.1: diphenylphosphoryl azide; Et₃N / dioxane / 1 h / 20 °C

5.2: dioxane / 0.5 h / Heating

6.1: p-TsOH; EtOH / 1 h / 40 °C

7.1: SO₃*Py; Et₃N / dimethylsulfoxide / 0.5 h / 20 °C

8.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

9.1: NaBH₄; NiCl₂ / tetrahydrofuran; methanol / 0.5 h / 20 °C

10.1: aq. NaOH / tetrahydrofuran; methanol / 2 h / 40 °C

11.1: 87 percent / EDCI; HOBt; N-methylmorpholine / dimethylformamide / 15 h / 20 °C

12.1: 79 percent / Lawesson's reagent / toluene / 6 h / Heating

13.1: NaH / dimethylformamide / 0.5 h / 0 °C

13.2: 100 percent / dimethylformamide / 1 h / 0 °C

With Lawessons reagent; 4-methyl-morpholine; sodium hydroxide; sodium tetrahydroborate; pyridine-SO₃ complex; ethanol; diphenylphosphoranyl azide; pyridinium p-toluenesulfonate; sodium hydride; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; calcium chloride; nickel dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 8.1: Horner-Emmons reaction;
DOI:10.1016/j.bmcl.2004.01.049