Acetyl chloride → HCID 67261450, compound

HRID 2359044Notes

Reaction equation

HRID 2359044 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[CH:13]=3)=[CH:10][N:9]([CH:19]([CH3:21])[CH3:20])[N:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30].C1C[O:36][CH2:35][CH2:34]1>>[C:29]([N:18]([C:14]1[CH:13]=[C:12]([C:11]2[C:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)=[N:8][N:9]([CH:19]([CH3:21])[CH3:20])[CH:10]=2)[CH:17]=[CH:16][N:15]=1)[C:35](=[O:36])[CH3:34])(=[O:31])[CH3:30]

Participants

5

Reactant 4

HCID 6367Acetyl chloride2×HCID 8028TetrahydrofuranHCID 8471Triethylamine2×HCID 67260517HCID 67260517, compound

Product 1

HCID 67261450HCID 67261450, compoundYield 81%

Procedure

To a solution of 4-[3-(5-chloro-2-thienyl)-1-isopropyl-1H-pyrazol-4-yl]pyridin-2-amine (1 eq, 0.31 mmol) and triethylamine (4 eq, 1.3 mmol) in 3 mL THF was added acetyl chloride (2.1 eq, 0.66 mmol). The mixture was then stirred at room temperature for 30 min. Acetyl chloride (1 eq, 0.31 mmol) and triethylamine (2 eq, 0.62 mmol) were then added and the mixture was stirred for 1 h. The solvent was evaporated and the residue was purified by chromatography on silica gel (heptane:ethyl acetate 5:1 to 1:2) to afford 114 mg of N-acetyl-N-{4-[3-(5-chloro-2-thienyl)-1-isopropyl-1H-pyrazol-4-yl]pyridin-2-yl}acetamide (81% yield).

Workup

  1. stirringthe mixture was stirred for 1 h
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography on silica gel (heptane:ethyl acetate 5:1 to 1:2)

Sources & evidence

ORD record
ord-139d55769b154f9c82e02820d2d91cb8
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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