Chloroacetyl chloride → HCID 66958505, compound

HRID 1364028Notes

Reaction equation

HRID 1364028 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:9][CH:8]=[CH:7][CH:6]=2.C(N(CC)CC)C.[Cl:30][CH2:31][C:32](Cl)=O>ClCCl>[Cl:30][CH2:31][C:32]1[N:12]([CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 12016824tert-Butyl 2-(3-aminoquinolin-4-ylamino)ethylcarbamate

Product 1

HCID 66958505HCID 66958505, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A modification of the method described in Part E of Example 1 was used to treat tert-butyl 2-[(3-aminoquinolin-4-yl)amino]ethylcarbamate (15.65 g, 51.76 mmol) with triethylamine (10.82 mL, 77.64 mmol) followed by chloroacetyl chloride (4.5 mL, 57 mmol). The reaction was carried out in dichloromethane (60 mL). After the reaction mixture was filtered, the filtrate was washed with dilute aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated under reduced pressure to provide tert-butyl 2-[2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamate as an amber-colored solid, which was combined with material from two other runs for use in the next step.

Workup

  1. filtrationAfter the reaction mixture was filtered
  2. washthe filtrate was washed with dilute aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7c1d5d6fd82f480e95afe213dc8c7192
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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