Chloroacetyl chloride → HCID 178432552, compound

HRID 1878077Notes

Reaction equation

HRID 1878077 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([OH:14])[C:11]([CH3:15])=[C:10]([CH3:16])[N:9]=2)=[N:6][CH:7]=1.C(N(CC)CC)C.[Cl:24][CH2:25][C:26](Cl)=[O:27]>C1COCC1>[Cl:24][CH2:25][C:26]([NH:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[N:13]=[C:12]([OH:14])[C:11]([CH3:15])=[C:10]([CH3:16])[N:9]=2)=[CH:4][CH:3]=1)=[O:27]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 178432546HCID 178432546, compound

Product 1

HCID 178432552HCID 178432552, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound of example 48 (0.04 g, 0.185 mmol) in THF (4 mL), at 0° C. was added triethylamine (0.028 g, 0.277 mmol) and chloroacetylchloride (0.0313 g, 0.277 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 using silica gel and 1% 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

Sources & evidence

ORD record
ord-d494166a42a242f588e95f355f07f76b
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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