Chloroacetyl chloride → HCID 66958693, compound

HRID 1364054Notes

Reaction equation

HRID 1364054 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]=[C:7]([Br:23])[CH:6]=2.C(N(CC)CC)C.[Cl:31][CH2:32][C:33](Cl)=O>C(O)C>[Br:23][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[C:33]([CH2:32][Cl:31])=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66957881HCID 66957881, compound

Product 1

HCID 66958693HCID 66958693, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A modification of the method described in Part C of Example 365 was used to treat tert-butyl 2-[(3-amino-7-bromoquinolin-4-yl)amino]ethylcarbamate (66.69 g, 174.9 mmol, U.S. patent application publication no. US 2004/0147543, Example 386, Parts A and B) with triethylamine (35.4 g, 350 mmol) and chloroacetyl chloride (20.7 g, 183 mmol). After the reaction in ethanol was complete, a precipitate was present and was isolated by filtration to provide 38.42 g of tert-butyl 2-[7-bromo-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamate as white crystals. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluting with 2 N ammonia in methanol/chloroform in a 33-minute gradient from 0:100 to 5:95) to provide an additional 4.89 g of product.

Workup

  1. customwas isolated by filtration

Sources & evidence

ORD record
ord-1fff4e41bba24bd39d78f6c09e760b27
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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