N₁-ethyl-3-[6-chloro-8-(3-fluorophenyl)-2-[2-(1-hydroxycyclohexyl)-1-ethynyl]-9H-9-purinyl]-1-propanesulfonamide

Base Information

• Chemical Name: N₁-ethyl-3-[6-chloro-8-(3-fluorophenyl)-2-[2-(1-hydroxycyclohexyl)-1-ethynyl]-9H-9-purinyl]-1-propanesulfonamide
• CAS No.: 391249-10-8
• Molecular Formula: C₂₄H₂₇ClFN₅O₃S
• Molecular Weight: 520.027

Synonyms:N₁-ethyl-3-[6-chloro-8-(3-fluorophenyl)-2-[2-(1-hydroxycyclohexyl)-1-ethynyl]-9H-9-purinyl]-1-propanesulfonamide

Chemical Property of N₁-ethyl-3-[6-chloro-8-(3-fluorophenyl)-2-[2-(1-hydroxycyclohexyl)-1-ethynyl]-9H-9-purinyl]-1-propanesulfonamide

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Technology Process of N₁-ethyl-3-[6-chloro-8-(3-fluorophenyl)-2-[2-(1-hydroxycyclohexyl)-1-ethynyl]-9H-9-purinyl]-1-propanesulfonamide

There total 8 articles about N₁-ethyl-3-[6-chloro-8-(3-fluorophenyl)-2-[2-(1-hydroxycyclohexyl)-1-ethynyl]-9H-9-purinyl]-1-propanesulfonamide 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%

1-Ethynylcyclohexan-1-ol (78-27-3) + N1-ethyl-3-[6-chloro-8-(3-fluorophenyl)-2-iodo-9H-9-purinyl]-1-propanesulfonamide (391249-09-5) → N1-ethyl-3-[6-chloro-8-(3-fluorophenyl)-2-[2-(1-hydroxycyclohexyl)-1-ethynyl]-9H-9-purinyl]-1-propanesulfonamide (391249-10-8)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0968-0896(01)00201-2

Reference yield:

N1-ethyl-3-chloro-1-propanesulfonamide (216487-29-5) → N1-ethyl-3-[6-chloro-8-(3-fluorophenyl)-2-[2-(1-hydroxycyclohexyl)-1-ethynyl]-9H-9-purinyl]-1-propanesulfonamide (391249-10-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 84 percent / NaI / butan-2-one / 6.5 h / Heating

2.1: 74 percent / NaN₃ / H₂O; methanol / 3 h / Heating

3.1: 95 percent / H₂ / Pd/C / methanol / 10 h / 20 °C

4.1: 54 percent / AcOH / methanol; tetrahydrofuran / 0 - 20 °C

5.1: 57 percent / H₂ / Raney nickel / methanol / 20 °C

6.1: acetic acid / methanol / 20 °C

6.2: FeCl₃ / ethanol / Heating

6.3: 32 percent / aq. HCl / tetrahydrofuran / Heating

7.1: 29 percent / isoamyl nitrite; CuI; CH₂I₂ / tetrahydrofuran / Heating

8.1: 81 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / tetrahydrofuran / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sodium azide; diiodomethane; hydrogen; acetic acid; triethylamine; sodium iodide; isopentyl nitrite; palladium on activated charcoal; nickel; In tetrahydrofuran; methanol; water; butanone;

DOI:10.1016/S0968-0896(01)00201-2

Reference yield:

N1-ethyl-3-iodo-1-propanesulfonamide (391249-03-9) → N1-ethyl-3-[6-chloro-8-(3-fluorophenyl)-2-[2-(1-hydroxycyclohexyl)-1-ethynyl]-9H-9-purinyl]-1-propanesulfonamide (391249-10-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 74 percent / NaN₃ / H₂O; methanol / 3 h / Heating

2.1: 95 percent / H₂ / Pd/C / methanol / 10 h / 20 °C

3.1: 54 percent / AcOH / methanol; tetrahydrofuran / 0 - 20 °C

4.1: 57 percent / H₂ / Raney nickel / methanol / 20 °C

5.1: acetic acid / methanol / 20 °C

5.2: FeCl₃ / ethanol / Heating

5.3: 32 percent / aq. HCl / tetrahydrofuran / Heating

6.1: 29 percent / isoamyl nitrite; CuI; CH₂I₂ / tetrahydrofuran / Heating

7.1: 81 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / tetrahydrofuran / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sodium azide; diiodomethane; hydrogen; acetic acid; triethylamine; isopentyl nitrite; palladium on activated charcoal; nickel; In tetrahydrofuran; methanol; water;

DOI:10.1016/S0968-0896(01)00201-2

upstream raw materials:

1-Ethynylcyclohexan-1-ol

N₁-ethyl-3-[6-chloro-8-(3-fluorophenyl)-2-iodo-9H-9-purinyl]-1-propanesulfonamide

N₁-ethyl-3-chloro-1-propanesulfonamide

N₁-ethyl-3-amino-1-propanesulfonamide

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