Acetyl chloride → HCID 21897749, compound

HRID 1958366Notes

Reaction equation

HRID 1958366 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[N:5]=[C:4]([CH3:17])[C:3]=1[C:18]#[N:19].[C:20](Cl)(=[O:22])[CH3:21]>>[C:18]([C:3]1[C:4]([CH3:17])=[N:5][N:6]([C:7]2[CH:8]=[CH:9][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:11][CH:12]=2)[C:2]=1[NH:1][C:20](=[O:22])[CH3:21])#[N:19]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 21897617HCID 21897617, compound

Product 1

HCID 21897749HCID 21897749, compoundYield 56%

Conditions

Temperature
60 °C

Procedure

To a 50 mL round-bottomed equipped with a reflux condenser and N2 inlet septum was placed a stir bar, 5-amino-1-(4-methanesulfonyl-phenyl)-3-methyl-1H-pyrazole-4-carbonitrile (85 mg, 0.31 mmol), and acetyl chloride (5 mL). The reaction mixture was stirred under N2 for 24 hrs at 60° C. The acetyl chloride was removed under reduced pressure and solid residue washed with CH2Cl2 and EtOAc and collected by filtration. The crude product was then purified by flash chromatography (EtOAc:Hex=1:1) and recrystallized from methanol. 55 mg of product was obtained (56% yield). 1H NMR (DMSO-d6, 400 MHz) δ 2.07 (s, 3H), 2.36 (s, 3H), 3.29 (s, 3H), 7.81 (d, 2H), 8.09 (d, 2H), 10.7 (s, 1H). LCMS: calculated C14H14N4O3S 318.08, observed 319.1 (MH+)

Workup

  1. customTo a 50 mL round-bottomed equipped with a reflux condenser and N2 inlet septum
  2. customThe acetyl chloride was removed under reduced pressure and solid residue
  3. washwashed with CH2Cl2 and EtOAc
  4. filtrationcollected by filtration
  5. customThe crude product was then purified by flash chromatography (EtOAc:Hex=1:1)
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-7c2d151961b24f298e9d77ce0613abb0
Source dataset
uspto-grants-2013_04
Patent number
US08410119B2

Reaction notes

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