Chloroacetyl chloride → HCID 25184910, compound

HRID 1878088Notes

Reaction equation

HRID 1878088 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:6]=[C:5]([C:13]2[N:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[N:4]=1.C(N(CC)CC)C.[Cl:27][CH2:28][C:29](Cl)=[O:30]>C1COCC1>[Cl:27][CH2:28][C:29]([NH:19][C:16]1[CH:17]=[N:18][C:13]([C:5]2[N:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:6]=2)=[CH:14][CH:15]=1)=[O:30]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 25184907HCID 25184907, compound

Product 1

HCID 25184910HCID 25184910, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cool (0° C.) solution of compound of example 59 (0.08 g, 0.296 mmol) in THF (5 mL) was added triethylamine (0.044 g, 0.44 mmol) and chloroacetylchloride (0.050 g, 0.44 mmol), and the reaction mixture was stirred at room temperature for 30 minutes. THF was removed under reduced pressure, and reaction mixture was quenched with water and extracted with ethyl acetate (3×10 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain the crude product, which was purified by column chromatography (silica gel, 50% ethyl acetate in petroleum ether as an eluent) to obtain the title compound.

Workup

  1. customTHF was removed under reduced pressure, and reaction mixture
  2. customwas quenched with water
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto obtain the crude product, which
  7. customwas purified by column chromatography (silica gel, 50% ethyl acetate in petroleum ether as an eluent)

Sources & evidence

ORD record
ord-b9855b50ab204be8b0cc7a3151f967c5
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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