Chloroacetyl chloride → HCID 66958478, compound

HRID 1364051Notes

Reaction equation

HRID 1364051 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]=[C:14]([Br:31])[CH:13]=2.[Cl:32][CH2:33][C:34](Cl)=O>ClCCl>[Br:31][C:14]1[CH:15]=[CH:16][C:17]2[C:18]3[N:19]([CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[C:34]([CH2:33][Cl:32])=[N:8][C:9]=3[CH:10]=[N:11][C:12]=2[CH:13]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66620332HCID 66620332, compound

Product 1

HCID 66958478HCID 66958478, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (26.7 g, 264 mmol) was added to a solution of tert-butyl 3-[(3-amino-7-bromoquinolin-4-yl)amino]propylcarbamate (52.17 g, 132.0 mmol) in dichloromethane (370 mL). Chloroacetyl chloride (15.65 g, 138.6 mmol) was added, and the reaction was stirred overnight at ambient temperature. The solvent was removed under reduced pressure, and the residue was stirred in ethanol (1 L) overnight at ambient temperature. The solvent was removed under reduced pressure, and the residue was dissolved in chloroform. The resulting solution was washed twice with water, concentrated under reduced pressure, and dried under high vacuum to provide 41.63 g of tert-butyl 3-[7-bromo-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propylcarbamate.

Workup

  1. customThe solvent was removed under reduced pressure
  2. stirringthe residue was stirred in ethanol (1 L) overnight at ambient temperature
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in chloroform
  5. washThe resulting solution was washed twice with water
  6. concentrationconcentrated under reduced pressure
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-a87affdf8b8a46978aaadd03bdfad4a9
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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