Chloroacetyl chloride → Methyl 2-(4-((N-(3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propyl)-2-(piperidin-1-yl)acetamido)methyl)phenyl)acetate

HRID 2090265Notes

Reaction equation

HRID 2090265 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:31][CH2:32][O:33][CH3:34])[N:14]([CH2:15][CH2:16][CH2:17][NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:22][CH:21]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl[CH2:36][C:37](Cl)=[O:38].[NH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>CC#N>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:31][CH2:32][O:33][CH3:34])[N:14]([CH2:15][CH2:16][CH2:17][N:18]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:24][CH:25]=3)[C:37](=[O:38])[CH2:36][N:40]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8082PiperidineHCID 68430910Methyl 2-(4-((3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propylamino)methyl)phenyl)acetate

Product 1

HCID 25107055Methyl 2-(4-((N-(3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propyl)-2-(piperidin-1-yl)acetamido)methyl)phenyl)acetateYield 9.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the product from step (v) (180 mg) in MeCN (5 mL), 2-chloroacetyl chloride (44.0 mg) was added at 0° C. and stirred for 7 h. Piperidine (332 mg) was added and stirred at rt for 15 h. The solvent was removed and the crude product was purified by RPHPLC. The resulting residue was triturated with diethyl ether to afford the title compound as a white solid (22 mg).

Workup

  1. stirringstirred at rt for 15 h
  2. customThe solvent was removed
  3. customthe crude product was purified by RPHPLC
  4. customThe resulting residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-96dbce1757e54364b6f887aa183c66cd
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

Loading…