N₂-{4-cyclopropyl-6-fluoro-3-[4-(trideuteriomethyl)-1,2,3,4-tetrazol-5-one-1-yl]}phenyl-5-fluoro-N₄-(2,2,6,6-tetramethylpiperidin-4-yl)-2,4-pyrimidinediamine

Base Information

• Chemical Name: N₂-{4-cyclopropyl-6-fluoro-3-[4-(trideuteriomethyl)-1,2,3,4-tetrazol-5-one-1-yl]}phenyl-5-fluoro-N₄-(2,2,6,6-tetramethylpiperidin-4-yl)-2,4-pyrimidinediamine
• CAS No.: 1309832-94-7
• Molecular Formula: C₂₄H₃₁F₂N₉O
• Molecular Weight: 502.543

Synonyms:N₂-{4-cyclopropyl-6-fluoro-3-[4-(trideuteriomethyl)-1,2,3,4-tetrazol-5-one-1-yl]}phenyl-5-fluoro-N₄-(2,2,6,6-tetramethylpiperidin-4-yl)-2,4-pyrimidinediamine

Chemical Property of N₂-{4-cyclopropyl-6-fluoro-3-[4-(trideuteriomethyl)-1,2,3,4-tetrazol-5-one-1-yl]}phenyl-5-fluoro-N₄-(2,2,6,6-tetramethylpiperidin-4-yl)-2,4-pyrimidinediamine

Chemical Property:

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Technology Process of N₂-{4-cyclopropyl-6-fluoro-3-[4-(trideuteriomethyl)-1,2,3,4-tetrazol-5-one-1-yl]}phenyl-5-fluoro-N₄-(2,2,6,6-tetramethylpiperidin-4-yl)-2,4-pyrimidinediamine

There total 8 articles about N₂-{4-cyclopropyl-6-fluoro-3-[4-(trideuteriomethyl)-1,2,3,4-tetrazol-5-one-1-yl]}phenyl-5-fluoro-N₄-(2,2,6,6-tetramethylpiperidin-4-yl)-2,4-pyrimidinediamine 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: 34.0%

1-(5-amino-2-cyclopropyl-4-fluorophenyl)-4-(trideuteriomethyl)-1H-tetrazol-5(4H)-one (1309832-93-6) + 2-chloro-5-fluoro-N4-(2,2,6,6-tetramethylpiperidin-4-yl)-4-pyrimidineamine hydrochloride → N2-{4-cyclopropyl-6-fluoro-3-[4-(trideuteriomethyl)-1,2,3,4-tetrazol-5-one-1-yl]}phenyl-5-fluoro-N4-(2,2,6,6-tetramethylpiperidin-4-yl)-2,4-pyrimidinediamine (1309832-94-7)

Guidance literature:

1-(5-amino-2-cyclopropyl-4-fluorophenyl)-4-(trideuteriomethyl)-1H-tetrazol-5(4H)-one; 2-chloro-5-fluoro-N₄-(2,2,6,6-tetramethylpiperidin-4-yl)-4-pyrimidineamine hydrochloride; With toluene-4-sulfonic acid; In isopropyl alcohol; for 48h; Reflux;

With meta-aminobenzoic acid; In isopropyl alcohol; Reflux;

With sodium hydroxide; In water; ethyl acetate;

Reference yield:

2-bromo-4-fluoroaniline (1003-98-1) → N2-{4-cyclopropyl-6-fluoro-3-[4-(trideuteriomethyl)-1,2,3,4-tetrazol-5-one-1-yl]}phenyl-5-fluoro-N4-(2,2,6,6-tetramethylpiperidin-4-yl)-2,4-pyrimidinediamine (1309832-94-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: nitric acid; sulfuric acid / 1.08 h / -20 - -15 °C

2.1: caesium carbonate / tricyclohexylphosphine; palladium diacetate / toluene; water / 100 °C / Inert atmosphere

3.1: toluene / 3.25 h / -10 - 80 °C / Inert atmosphere

4.1: trimethylsilylazide / 80 °C / Inert atmosphere

5.1: potassium carbonate / N,N-dimethyl-formamide / -78 - 20 °C / Inert atmosphere

6.1: hydrogen / palladium on carbon / ethanol / 1551.49 Torr

7.1: toluene-4-sulfonic acid / isopropyl alcohol / 48 h / Reflux

7.2: Reflux

With trimethylsilylazide; sulfuric acid; hydrogen; nitric acid; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; palladium on carbon; palladium diacetate; tricyclohexylphosphine; In ethanol; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 2.1: Suzuki Coupling;

Reference yield:

2-bromo-4-fluoro-5-nitrophenylamine (346433-97-4) → N2-{4-cyclopropyl-6-fluoro-3-[4-(trideuteriomethyl)-1,2,3,4-tetrazol-5-one-1-yl]}phenyl-5-fluoro-N4-(2,2,6,6-tetramethylpiperidin-4-yl)-2,4-pyrimidinediamine (1309832-94-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: caesium carbonate / tricyclohexylphosphine; palladium diacetate / toluene; water / 100 °C / Inert atmosphere

2.1: toluene / 3.25 h / -10 - 80 °C / Inert atmosphere

3.1: trimethylsilylazide / 80 °C / Inert atmosphere

4.1: potassium carbonate / N,N-dimethyl-formamide / -78 - 20 °C / Inert atmosphere

5.1: hydrogen / palladium on carbon / ethanol / 1551.49 Torr

6.1: toluene-4-sulfonic acid / isopropyl alcohol / 48 h / Reflux

6.2: Reflux

With trimethylsilylazide; hydrogen; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; palladium on carbon; palladium diacetate; tricyclohexylphosphine; In ethanol; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 1.1: Suzuki Coupling;

upstream raw materials:

4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE

2-bromo-4-fluoroaniline

2-bromo-4-fluoro-5-nitrophenylamine

2-Cyclopropyl-4-fluoro-5-nitroaniline

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