Chloroacetyl chloride → HCID 25184849, compound

HRID 1878083Notes

Reaction equation

HRID 1878083 reaction equation
[CH2:1]([O:4][C:5]1[C:10]([Cl:11])=[C:9]([CH3:12])[N:8]=[C:7]([C:13]2[N:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[N:6]=1)[CH:2]=[CH2:3].C(N(CC)CC)C.[Cl:27][CH2:28][C:29](Cl)=[O:30]>C1COCC1>[CH2:1]([O:4][C:5]1[C:10]([Cl:11])=[C:9]([CH3:12])[N:8]=[C:7]([C:13]2[N:18]=[CH:17][C:16]([NH:19][C:29](=[O:30])[CH2:28][Cl:27])=[CH:15][CH:14]=2)[N:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 25184908HCID 25184908, compound

Product 1

HCID 25184849HCID 25184849, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound of example 55 (0.064 g, 0.231 mmol) in THF (4 mL), at 0° C. was added triethylamine (0.035 g, 0.346 mmol) and chloroacetylchloride (0.039 g, 0.346 mmol), and the reaction mixture was stirred at room temperature for 30 minutes. THF was removed under reduced pressure, and the 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 using silica gel and 1% methanol in chloroform as an eluent to obtain the title compound.

Workup

  1. customTHF was removed under reduced pressure
  2. customthe reaction mixture was 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

Sources & evidence

ORD record
ord-80c27dd06c64468b96afb281723e55b5
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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