(2S)-1-[(3R)-12-[[4-(dimethylamino)cyclohexyl]amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-3-yl]propan-2-ol formate

Base Information

• Chemical Name: (2S)-1-[(3R)-12-[[4-(dimethylamino)cyclohexyl]amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-3-yl]propan-2-ol formate
• CAS No.: 1388894-27-6
• Molecular Formula: CH₂O₂*C₂₀H₃₀N₄OS
• Molecular Weight: 420.576

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

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

Chemical Property:

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

There total 14 articles about (2S)-1-[(3R)-12-[[4-(dimethylamino)cyclohexyl]amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-3-yl]propan-2-ol formate 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) + 1-[(3R)-12-[(4-aminocyclohexyl)amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]propan-2-ol (1388894-29-8) → (2S)-1-[(3R)-12-[[4-(dimethylamino)cyclohexyl]amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]propan-2-ol formate (1388894-27-6) + (2R)-1-[(3R)-12-[[4-(dimethylamino)cyclohexyl]amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]propan-2-ol formate (1388894-25-4)

Guidance literature:

formaldehyd; 1-[(3R)-12-[(4-aminocyclohexyl)amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-3-yl]propan-2-ol; In methanol; at 20 ℃; for 1h;

With sodium cyanoborohydride; In methanol; at 20 ℃; for 2h;

With formic acid; In water; acetonitrile;

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + formic acid (64-18-6) + 1-[(3R)-12-[(4-aminocyclohexyl)amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]propan-2-ol (1388894-29-8) → (2S)-1-[(3R)-12-[[4-(dimethylamino)cyclohexyl]amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]propan-2-ol formate (1388894-27-6) + (2R)-1-[(3R)-12-[[4-(dimethylamino)cyclohexyl]amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]propan-2-ol formate (1388894-25-4)

Guidance literature:

formaldehyd; 1-[(3R)-12-[(4-aminocyclohexyl)amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-3-yl]propan-2-ol; In methanol; at 20 ℃; for 1h;

With methanol; sodium cyanoborohydride; at 20 ℃; for 2h;

formic acid; In acetonitrile;

Reference yield:

ethyl 2-[12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]acetate (1388893-77-3) → (2S)-1-[(3R)-12-[[4-(dimethylamino)cyclohexyl]amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]propan-2-ol formate (1388894-27-6) + (2R)-1-[(3R)-12-[[4-(dimethylamino)cyclohexyl]amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]propan-2-ol formate (1388894-25-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: diisobutylaluminium hydride / hexane; tetrahydrofuran / -30 °C / Inert atmosphere

2.1: CHIRALPAK IA / carbon dioxide; methanol / Resolution of racemate

3.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

4.1: triethylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

4.2: 14 h / 50 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

6.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C

7.1: tetrahydrofuran / 0 °C / Inert atmosphere

7.2: Inert atmosphere

8.1: hydrogenchloride / dichloromethane / 0 - 20 °C

8.2: pH 8

9.1: methanol / 1 h / 20 °C

9.2: 2 h / 20 °C

With 1H-imidazole; hydrogenchloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; carbon dioxide; N,N-dimethyl-formamide;

upstream raw materials:

formaldehyd

1-[(3R)-12-[(4-aminocyclohexyl)amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-3-yl]propan-2-ol

trans-N-Boc-1,4-cyclohexanediamine

ethyl (2-oxocyclopentyl)acetate

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