Acetyl chloride → N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)acetamide

HRID 512700Notes

Reaction equation

HRID 512700 reaction equation
[Cl:1][C:2]1[C:6]([NH2:7])=[CH:5][N:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1.[C:14](Cl)(=[O:16])[CH3:15].C(OC(=O)C)(=O)C>>[Cl:1][C:2]1[C:6]([NH:7][C:14](=[O:16])[CH3:15])=[CH:5][N:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 7918Acetic Anhydride2×HCID 674993943-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-amine

Product 1

HCID 118023019N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)acetamide

Procedure

In step g of Scheme 1, 3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-amine (5d) is acylated with acetylating agents such as acetyl chloride or acetic anhydride, preferably acetic anhydride (Ac2O) to yield N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)acetamide (1c). The acylation is conducted in the presence of a base, preferably an inorganic base, such as, sodium bicarbonate (NaHCO3), and preferably, a polar solvent, such as ethyl acetate and/or tetrahydrofuran. This reaction may be conducted at temperatures from about −10° C. to about 30° C.

Sources & evidence

ORD record
ord-c9c92a5cff8943c9809272620994c5e9
Source dataset
uspto-grants-2015_08
Patent number
US09102654B2

Reaction notes

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