Acetyl chloride → HCID 58966901, compound

HRID 1948233Notes

Reaction equation

HRID 1948233 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][NH2:22])=[CH:15][CH:14]=3)[CH:10]=[CH:9][C:8]2=[O:23])=[C:4]([F:26])[CH:3]=1.CCN(CC)CC.[C:34](Cl)(=[O:36])[CH3:35]>C(Cl)Cl>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:8](=[O:23])[CH:9]=[CH:10][C:11]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][NH:22][C:34](=[O:36])[CH3:35])=[CH:17][CH:18]=3)=[CH:12]2)=[C:4]([F:26])[CH:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 69349078HCID 69349078, compound

Product 1

HCID 58966901HCID 58966901, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to Scheme 19 Step 3: To a solution of 1-(4-chloro-2-fluorobenzyl)-5-(4-(2-aminoethoxy)phenyl)pyridin-2(1H)-one (1 eq, 0.18 mmol, 0.07 g) in CH2Cl2 (5 mL) at 0° C. were added Et3N (6 eq, 1.10 mmol, 0.15 mL) and 30 min. later acetyl chloride (1.5 eq, 0.27 mmol, 19 μL) and. The reaction mixture was stirred 1 hour at room temperature. The reaction mixture was quenched with water and extracted with CH2Cl2. The organic phase was dried over Na2SO4, filtered and evaporated. The crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2, CH2Cl2/AcOEt 70/30) to afford N-(2-(4-(1-(4-chloro-2-fluorobenzyl)-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)ethyl)acetamide (0.08 mmol, 0.04 g, 47%) as a white solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2, CH2Cl2/AcOEt 70/30)

Sources & evidence

ORD record
ord-c9d63d8bcc7d41bbb4a2b015c5c8e1ff
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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