Chloroacetyl chloride → HCID 66958446, compound

HRID 2383221Notes

Reaction equation

HRID 2383221 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][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:16][CH:15]=[C:14]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:13]=2.[Cl:38][CH2:39][C:40](Cl)=O>ClCCl>[CH2:31]([O:30][C:14]1[CH:15]=[CH:16][C:17]2[C:18]3[N:19]([CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:40]([CH2:39][Cl:38])=[N:8][C:9]=3[CH:10]=[N:11][C:12]=2[CH:13]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66958391Tert-butyl 2-[(3-amino-7-benzyloxyquinolin-4-yl)amino]ethylcarbamate

Product 1

HCID 66958446HCID 66958446, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (24.0 mL, 172.58 mmol) was added to a solution of tert-butyl 2-[(3-amino-7-benzyloxyquinolin-4-yl)amino]ethylcarbamate (35.25 g, 86.29 mmol) in dichloromethane (400 mL) and stirred at ambient temperature. Chloroacetyl chloride (6.87 mL, 86.29 mmol) was quickly added at ambient temperature to avoid splashing and was stirred for 10 minutes. The reaction mixture was concentrated under reduced pressure, dissolved in ethanol (500 mL), and stirred for 2 days at ambient temperature. The mixture was concentrated under reduced pressure and the residue was recrystallized from dichloromethane to afford 6.23 g of tert-butyl 2-(7-benzyloxy-2-chloromethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethylcarbamate.

Workup

  1. stirringwas stirred for 10 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutiondissolved in ethanol (500 mL)
  4. stirringstirred for 2 days at ambient temperature
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customthe residue was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-7f53f9875a3147c69c552fd0eaf82b57
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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