Chloroacetyl chloride → HCID 66958143, compound

HRID 1364018Notes

Reaction equation

HRID 1364018 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][CH:21]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[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:39][CH2:40][C:41](Cl)=O>ClCCCl>[Si:32]([O:31][CH:21]([CH2:20][N:19]1[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]=[C:41]1[CH2:40][Cl:39])[CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66958490HCID 66958490, compound

Product 1

HCID 66958143HCID 66958143, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Triethylamine (46.2 g, 456 mmol) was added to a solution of tert-butyl 3-[(3-aminoquinolin-4-yl)amino]-2-{[tert-butyl(dimethyl)silyl]oxy}propylcarbamate (101.9 g, 228.1 mmol) in 1,2-dichloroethane (600 mL). A solution of chloroacetyl chloride (28.3 g, 251 mmol) in 1,2-dichloroethane was added dropwise, and the reaction was stirred overnight at ambient temperature. The reaction mixture was filtered to remove a solid, and the filtrate was concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting sequentially with 95.5:0.5 and 95:5 dichloromethane:methanol), and the purified product was dried overnight under high vacuum to provide 71.93 g of tert-butyl 2-{[tert-butyl(dimethyl)silyl]oxy}-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. customThe crude product was purified by column chromatography on silica gel (
  5. washeluting sequentially with 95.5:0.5 and 95:5 dichloromethane
  6. dry with materialmethanol), and the purified product was dried overnight under high vacuum

Sources & evidence

ORD record
ord-93939530d2474aa7a4c98126806e276e
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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