Chloroacetyl chloride → HCID 178432553, compound

HRID 1878095Notes

Reaction equation

HRID 1878095 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([OH:14])[C:11]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]([CH3:22])[N:9]=2)=[N:6][CH:7]=1.C(N(CC)CC)C.[Cl:30][CH2:31][C:32](Cl)=[O:33]>C1COCC1>[CH2:15]([C:11]1[C:12]([OH:14])=[N:13][C:8]([C:5]2[N:6]=[CH:7][C:2]([NH:1][C:32](=[O:33])[CH2:31][Cl:30])=[CH:3][CH:4]=2)=[N:9][C:10]=1[CH3:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 178432547HCID 178432547, compound

Product 1

HCID 178432553HCID 178432553, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) solution of compound of example 54 (0.050 g, 0.17 mmol) in THF (3 mL), was added triethylamine (0.025 g, 0.25 mmol) and chloroacetylchloride (0.029 g, 0.25 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, 5% methanol in chloroform 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, 5% methanol in chloroform as an eluent)

Sources & evidence

ORD record
ord-9cf4b624ae0143beae027dc6ae8b103d
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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