2-[(3S)-12-[[4-(dimethylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-3-yl]ethan-1-ol

Base Information

• Chemical Name: 2-[(3S)-12-[[4-(dimethylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-3-yl]ethan-1-ol
• CAS No.: 1388893-78-4
• Molecular Formula: C₁₉H₂₇N₃O₂S
• Molecular Weight: 361.508

Synonyms:2-[(3S)-12-[[4-(dimethylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-3-yl]ethan-1-ol

Chemical Property of 2-[(3S)-12-[[4-(dimethylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-3-yl]ethan-1-ol

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Technology Process of 2-[(3S)-12-[[4-(dimethylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-3-yl]ethan-1-ol

There total 7 articles about 2-[(3S)-12-[[4-(dimethylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-3-yl]ethan-1-ol 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:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + tert-butyl N-(4-[[(3S)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1(12),2(6),8,10-tetraen-12-yl]oxy]cyclohexyl)carbamate (1388893-83-1) → 2-[(3S)-12-[[4-(dimethylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]ethan-1-ol (1388893-78-4)

Guidance literature:

With formic acid; In methanol; at 20 - 100 ℃; Inert atmosphere;

Reference yield:

ethyl (2-oxocyclopentyl)acetate (20826-94-2) → 2-[(3S)-12-[[4-(dimethylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]ethan-1-ol (1388893-78-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: diethylamine; sulfur / ethanol / 20 °C

2.1: 20 - 180 °C / Inert atmosphere

2.2: Cooling with ice

3.1: CHIRALPAK IC / ethanol / Resolution of racemate

4.1: trichlorophosphate / 1,4-dioxane / 4 h / 110 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

6.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

6.2: Inert atmosphere

7.1: formic acid / methanol / 20 - 100 °C / Inert atmosphere

With lithium aluminium tetrahydride; formic acid; sodium hydride; sulfur; diethylamine; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; mineral oil;

Reference yield:

ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate (1029689-54-0) → 2-[(3S)-12-[[4-(dimethylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]ethan-1-ol (1388893-78-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 20 - 180 °C / Inert atmosphere

1.2: Cooling with ice

2.1: CHIRALPAK IC / ethanol / Resolution of racemate

3.1: trichlorophosphate / 1,4-dioxane / 4 h / 110 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

5.2: Inert atmosphere

6.1: formic acid / methanol / 20 - 100 °C / Inert atmosphere

With lithium aluminium tetrahydride; formic acid; sodium hydride; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; mineral oil;

upstream raw materials:

formaldehyd

tert-butyl N-(4-[[(3S)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-12-yl]oxy]cyclohexyl)carbamate

ethyl (2-oxocyclopentyl)acetate

ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate

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