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478081-98-0

478081-98-0

Identification

  • Product Name:Acetamide, N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethyl-

  • CAS Number: 478081-98-0

  • EINECS:

  • Molecular Weight:305.339

  • Molecular Formula: C17H15N5O

  • HS Code:

  • Mol File:478081-98-0.mol

Synonyms:Isozaleplon;Zaleplon related compound B;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:N-(3-(3-Cyanopyrazolo[1,5-α]pyrimidin-5-yl)phenyl)-N-ethylacetamide
  • Packaging:10mg
  • Price:$ 760
  • Delivery:In stock
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Relevant articles and documentsAll total 5 Articles be found

Synthetic studies connected with the preparation of N-[3-(3- cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethylacetamide, a zaleplon regioisomer

Radl, Stanislav,Blahovcova, Michaela,Tkadlecova, Marcela,Havlicek, Jaroslav

scheme or table, p. 1359 - 1376 (2010/10/20)

N-[3-(3-Cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethyl-acetamide, a principal impurity of zaleplon, is prepared by Suzuki-Miyaura cross coupling reaction of the corresponding boronic acid and/or boronates with 5-chloropyrazolo[1,5-a]pyrimidin-3-carbonitrile (7). Various methods of preparation of both components are described, as well as approaches based on the final modification of the 5-(3-aminophenyl)-pyrazolo[1,5-a]pyrimidine-3- carbonitrile moiety prepared by Suzuki-Miyaura cross coupling. All the prepared compounds were unambiguouesly identified by NMR techniques. Spectral characteristics (IR, UV, MS) of these compounds are also given.

N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethylacetamide and crystalline forms of zaleplon

-

, (2008/06/13)

Zaleplon crystalline Forms II, III, IV and V are useful for the treatment of insomnia. These crystalline Forms are described along with processes for making them by crystallization from selected solvents. A regioisomer of zaleplon is useful as a reference

Process for purifying N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide (zaleplon) and crystalline forms of zaleplon accessible with the process

-

, (2008/06/13)

Zaleplon can be separated from a regioisomer impurity by crystallization from selected solvents or by adding an anti-solvent to a solution of zaleplon and the regioisomer. Zaleplon crystalline Forms II, III, IV, and V are useful for the treatment of insom

Process for the production of N-[3-(3-cyanopyrazolo[1,5-a] pyrimidin-7-yl) phenyl]-N-ethylacetamide (zaleplon)

-

, (2008/06/13)

The present invention provides a process for the production of N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide (zaleplon), an active ingredient that is approved for the treatment of insomnia. The process involves reacting N-[3-[3-(dime

A PROCESS FOR THE PREPARATION OF ZALEPLON

-

Page 4; 5, (2008/06/13)

The invention relates to a process for the preparation of zaleplon (N-[3(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethyl-acetamide) in the reaction of 3-dimethylamino-1-(3-N-ethyl-N-acetylaminophenyl)-2-propen-1-one with 3-aminopyrazole-4-carbonitril

Process route upstream and downstream products

Process route

N-[3-[3-(dimethylamine)-1-oxo-2-propenyl]phenyl]-N-ethyl-acetamide
1227694-96-3

N-[3-[3-(dimethylamine)-1-oxo-2-propenyl]phenyl]-N-ethyl-acetamide

3-amino-4-cyano-2H-pyrazole
16617-46-2

3-amino-4-cyano-2H-pyrazole

N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide
478081-98-0

N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide

zaleplon
151319-34-5

zaleplon

Conditions
Conditions Yield
With formic acid; In water; at 10 - 40 ℃; for 3h; Product distribution / selectivity;
86%
With acetic acid; In water; Product distribution / selectivity;
58%
With propionic acid; In water; Product distribution / selectivity;
34%
N-[3-[3-(dimethylamine)-1-oxo-2-propenyl]phenyl]-N-ethyl-acetamide
1227694-96-3

N-[3-[3-(dimethylamine)-1-oxo-2-propenyl]phenyl]-N-ethyl-acetamide

3-Amino-4-cyanopyrazole
16617-46-2,882231-01-8

3-Amino-4-cyanopyrazole

N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide
478081-98-0

N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide

Conditions
Conditions Yield
With hydrogenchloride; In chloroform; water; acetone;
240 mg (4%)
With hydrogenchloride; In chloroform; water; acetone;
240 mg (4%)
5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile
1224288-95-2

5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

N-ethyI-N-(3-(4,4,5,5-tetramethyI-1,3,2-dioxaboroIan-2-yl)phenyI)acetamide
1224288-99-6

N-ethyI-N-(3-(4,4,5,5-tetramethyI-1,3,2-dioxaboroIan-2-yl)phenyI)acetamide

N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide
478081-98-0

N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide

Conditions
Conditions Yield
5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile; With triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In 1,4-dioxane; for 2h; Inert atmosphere; Sealed tube;
N-ethyI-N-(3-(4,4,5,5-tetramethyI-1,3,2-dioxaboroIan-2-yl)phenyI)acetamide; With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; at 20 ℃; Sealed tube;
75.8%
5-chloropyrazolo[1,5-a]pyrimidine-3-carbonitrile
1224288-92-9

5-chloropyrazolo[1,5-a]pyrimidine-3-carbonitrile

N-ethyI-N-(3-(4,4,5,5-tetramethyI-1,3,2-dioxaboroIan-2-yl)phenyI)acetamide
1224288-99-6

N-ethyI-N-(3-(4,4,5,5-tetramethyI-1,3,2-dioxaboroIan-2-yl)phenyI)acetamide

N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide
478081-98-0

N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide

Conditions
Conditions Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In toluene; at 100 ℃; for 10h;
81.9%
N-[3-[3-(dimethylamine)-1-oxo-2-propenyl]phenyl]-N-ethyl-acetamide
1227694-96-3

N-[3-[3-(dimethylamine)-1-oxo-2-propenyl]phenyl]-N-ethyl-acetamide

3-Amino-4-cyanopyrazole
16617-46-2,882231-01-8

3-Amino-4-cyanopyrazole

N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide
478081-98-0

N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide

zaleplon
151319-34-5

zaleplon

Conditions
Conditions Yield
With hydrogenchloride; In water;
N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)acetamide
1224289-08-0

N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)acetamide

ethyl iodide
75-03-6

ethyl iodide

N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide
478081-98-0

N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide

Conditions
Conditions Yield
N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)acetamide; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
ethyl iodide; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
55.7%
N-{3-[3-(dimethylamino)prop-2-enoyl]phenyl}-N-ethylacetamide
96605-66-2,1227694-96-3

N-{3-[3-(dimethylamino)prop-2-enoyl]phenyl}-N-ethylacetamide

3-amino-4-cyano-2H-pyrazole
16617-46-2

3-amino-4-cyano-2H-pyrazole

N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide
478081-98-0

N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide

zaleplon
151319-34-5

zaleplon

Conditions
Conditions Yield
With hydrogenchloride; In ethanol; water;

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