2,5-Dioxopyrrolidin-1-yl 3-(tritylthio)propanoate → N-{6-[(4-amino-2-(ethoxymethyl)-1-{2-methyl-2-[(methylsulfonyl)amino]propyl}-1H-imidazo[4,5-c]quinolin-7-yl)oxy]hexyl}-3-(tritylthio)propanamide

HRID 1845723Notes

Reaction equation

HRID 1845723 reaction equation
[C:1]1([C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:8][CH2:9][CH2:10][C:11](ON2C(=O)CCC2=O)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:33][C:34]1[C:43]2[N:44]=[C:45]([CH2:56][O:57][CH2:58][CH3:59])[N:46]([CH2:47][C:48]([NH:51][S:52]([CH3:55])(=[O:54])=[O:53])([CH3:50])[CH3:49])[C:42]=2[C:41]2[CH:40]=[CH:39][C:38]([OH:60])=[CH:37][C:36]=2[N:35]=1>CN(C=O)C.C(OCC)(=O)C>[NH2:33][C:34]1[C:43]2[N:44]=[C:45]([CH2:56][O:57][CH2:58][CH3:59])[N:46]([CH2:47][C:48]([CH3:50])([NH:51][S:52]([CH3:55])(=[O:54])=[O:53])[CH3:49])[C:42]=2[C:41]2[CH:40]=[CH:39][C:38]([O:60][CH2:37][CH2:36][CH2:41][CH2:42][CH2:43][CH2:34][NH:33][C:11](=[O:12])[CH2:10][CH2:9][S:8][C:7]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:37][C:36]=2[N:35]=1

Participants

5

Reactant 2

HCID 179354262,5-Dioxopyrrolidin-1-yl 3-(tritylthio)propanoateHCID 136075196N-[2-(4-amino-2-ethoxymethyl-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide

Product 1

HCID 68924374N-{6-[(4-amino-2-(ethoxymethyl)-1-{2-methyl-2-[(methylsulfonyl)amino]propyl}-1H-imidazo[4,5-c]quinolin-7-yl)oxy]hexyl}-3-(tritylthio)propanamideYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Succinimido 3-(triphenylmethylthio)propanoate (246 mg, 0.553 mmol) was added to a 0° C. solution of N-{2-[4-amino-2-(ethoxymethyl)-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide (280 mg, 0.553 mmol) in DMF (5 mL). The solution was stirred at 0° C. for 3 hours, then was diluted with ethyl acetate (100 mL) and washed with water (3×20 mL) and brine (40 mL). The organic phase was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by HPFC on silica gel (gradient elution with 2-50% CMA in chloroform) to provide 0.22 g of N-{6-[(4-amino-2-(ethoxymethyl)-1-{2-methyl-2-[(methylsulfonyl)amino]propyl}-1H-imidazo[4,5-c]quinolin-7-yl)oxy]hexyl}-3-(tritylthio)propanamide as a white solid.

Workup

  1. washwashed with water (3×20 mL) and brine (40 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by HPFC on silica gel (gradient elution with 2-50% CMA in chloroform)

Sources & evidence

ORD record
ord-2522c3fa799d48bab76af5742e63f35d
Source dataset
uspto-grants-2015_02
Patent number
US08951528B2

Reaction notes

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