Chloroacetyl chloride → HCID 66958458, compound

HRID 1364034Notes

Reaction equation

HRID 1364034 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[NH:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:16][CH:15]=[CH:14][CH:13]=2.[Cl:31][CH2:32][C:33](Cl)=O>ClCCl>[Cl:31][CH2:32][C:33]1[N:19]([CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:8]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66958404HCID 66958404, compound

Product 1

HCID 66958458HCID 66958458, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (20.4 g, 202 mmol) was added to a solution of tert-butyl 3-[(3-aminoquinolin-4-yl)amino]propylcarbamate (42.52 g, 134.4 mmol) in dichloromethane (500 mnL). Chloroacetyl chloride (16.7 g, 148 mmol) was added dropwise, and the reaction was stirred overnight at ambient temperature. The reaction mixture was filtered to remove a solid; the filtrate was concentrated under reduced pressure and mixed with ethyl acetate. The resulting mixture was filtered to remove a solid, washed sequentially with brine (3×) and dilute aqueous sodium bicarbonate, concentrated under reduced pressure, and dried under high vacuum to provide 41.9 g of tert-butyl 3-[2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propylcarbamate.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove a solid
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionmixed with ethyl acetate
  5. filtrationThe resulting mixture was filtered
  6. customto remove a solid
  7. washwashed sequentially with brine (3×) and dilute aqueous sodium bicarbonate
  8. concentrationconcentrated under reduced pressure
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-a1d04583c1f54c7aa64bfd57badf27c4
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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