1-{4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-1H-pyrazole-4-carboxylic acid amide

Base Information

• Chemical Name: 1-{4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-1H-pyrazole-4-carboxylic acid amide
• CAS No.: 219664-22-9
• Molecular Formula: C₁₆H₁₆FN₅O₄
• Molecular Weight: 361.333

Synonyms:1-{4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-1H-pyrazole-4-carboxylic acid amide

Chemical Property of 1-{4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-1H-pyrazole-4-carboxylic acid amide

Chemical Property:

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Technology Process of 1-{4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-1H-pyrazole-4-carboxylic acid amide

There total 11 articles about 1-{4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-1H-pyrazole-4-carboxylic acid amide 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-{4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-1H-pyrazole-4-carboxylic acid ethyl ester (219664-21-8) → 1-{4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-1H-pyrazole-4-carboxylic acid amide (219664-22-9)

Guidance literature:

With potassium cyanide; ammonia; In methanol; at 70 ℃;

DOI:10.1021/jm980546k

Reference yield:

3,4-difluoronitrobenzene (369-34-6) → 1-{4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-1H-pyrazole-4-carboxylic acid amide (219664-22-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 94 percent / hydrazine hydrate; K₂CO₃ / acetonitrile

2.1: 65 percent / NaOAc / ethanol / Heating

3.1: 97 percent / H₂ / 10percent Pd/C / methanol / 3 h / 1034.32 Torr

4.1: 98 percent / NaHCO₃ / tetrahydrofuran / 0 - 20 °C

5.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.75 h / -78 °C

5.2: 79 percent / tetrahydrofuran / -78 - 20 °C

6.1: 98 percent / NEt₃ / CH₂Cl₂ / 4 h / 20 °C

7.1: 93 percent / NaN₃ / dimethylformamide / 65 °C

8.1: 77 percent / triphenylphosphine; water / tetrahydrofuran / 20 - 65 °C

9.1: 99 percent / pyridine / CH₂Cl₂ / 20 °C

10.1: 34 percent / NH₃; KCN / methanol / 24 h / 70 °C

With pyridine; potassium cyanide; sodium azide; ammonia; water; hydrogen; sodium acetate; sodium hydrogencarbonate; potassium carbonate; hydrazine hydrate; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; 10percent Pd/C; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Substitution / 2.1: Condensation / 3.1: Reduction / 4.1: Acylation / 5.1: Metallation / 5.2: Ring cleavage / 6.1: mesylation / 7.1: Substitution / 8.1: Reduction / 9.1: Acetylation / 10.1: ammonolysis;

DOI:10.1021/jm990373e

Reference yield:

3-fluoro-1-nitro-4-(1H-4-carbethoxypyrazol-1-yl)benzene (219664-16-1) → 1-{4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-1H-pyrazole-4-carboxylic acid amide (219664-22-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 97 percent / H₂ / 10percent Pd/C / methanol / 3 h / 1034.32 Torr

2.1: 98 percent / NaHCO₃ / tetrahydrofuran / 0 - 20 °C

3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.75 h / -78 °C

3.2: 79 percent / tetrahydrofuran / -78 - 20 °C

4.1: 98 percent / NEt₃ / CH₂Cl₂ / 4 h / 20 °C

5.1: 93 percent / NaN₃ / dimethylformamide / 65 °C

6.1: 77 percent / triphenylphosphine; water / tetrahydrofuran / 20 - 65 °C

7.1: 99 percent / pyridine / CH₂Cl₂ / 20 °C

8.1: 34 percent / NH₃; KCN / methanol / 24 h / 70 °C

With pyridine; potassium cyanide; sodium azide; ammonia; water; hydrogen; sodium hydrogencarbonate; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Acylation / 3.1: Metallation / 3.2: Ring cleavage / 4.1: mesylation / 5.1: Substitution / 6.1: Reduction / 7.1: Acetylation / 8.1: ammonolysis;

DOI:10.1021/jm990373e

upstream raw materials:

1-{4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-1H-pyrazole-4-carboxylic acid ethyl ester

3,4-difluoronitrobenzene

(2-fluoro-4-nitrophenyl)hydrazine

ethyl 1-(4-amino-2-fluoro-phenyl)-1H-pyrazole-4-carboxylate

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