Chloroacetyl chloride → HCID 25184913, compound

HRID 1878089Notes

Reaction equation

HRID 1878089 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[N:7]=[C:6]([C:14]2[N:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[N:5]=1)[CH3:2].C(N(CC)CC)C.[Cl:28][CH2:29][C:30](Cl)=[O:31]>C1COCC1>[Cl:28][CH2:29][C:30]([NH:20][C:17]1[CH:18]=[N:19][C:14]([C:6]2[N:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:9]=[C:8]([C:10]([F:11])([F:13])[F:12])[N:7]=2)=[CH:15][CH:16]=1)=[O:31]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 25184848HCID 25184848, compound

Product 1

HCID 25184913HCID 25184913, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cool (0° C.) solution of compound of example 58 (0.04 g, 0.14 mmol) in THF (3 mL) was added triethylamine (0.021 g, 0.21 mmol) and chloroacetylchloride (0.023 g, 0.21 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-72a2ba85cceb45f4b3bf30fba423ccca
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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