Sodium Carbonate → N-{4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-ylmethyl]benzyl}methanesulfonamide

HRID 9495Notes

Reaction equation

HRID 9495 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH2:7][C:8]1[CH:38]=[CH:37][C:11]([CH2:12][N:13]2[C:25]3[C:24]4[CH:23]=[CH:22][C:21]([C:26]5[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=5)=[CH:20][C:19]=4[N:18]=[C:17]([NH2:32])[C:16]=3[N:15]=[C:14]2[CH2:33][O:34][CH2:35][CH3:36])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[NH2:32][C:17]1[C:16]2[N:15]=[C:14]([CH2:33][O:34][CH2:35][CH3:36])[N:13]([CH2:12][C:11]3[CH:10]=[CH:9][C:8]([CH2:7][NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:38][CH:37]=3)[C:25]=2[C:24]2[CH:23]=[CH:22][C:21]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:20][C:19]=2[N:18]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 219840501-(4-aminomethylbenzyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 21984108N-{4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-ylmethyl]benzyl}methanesulfonamideYield 38.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.13 mL, 1.7 mmol) was added dropwise to a mixture of 1-(4-aminomethylbenzyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine (0.520 g, 1.2 mmol) in dichloromethane (10 mL). The reaction was stirred for 16 hours and then saturated aqueous sodium carbonate was added. The layers were separated and the aqueous fraction was extracted with 95:5 chloroform/methanol. The organic fractions were combined and washed sequentially with water and saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was purified by flash column chromatography with a gradient of CMA (2%–10%) in chloroform as the eluent. A final recrystallization from 2-propanol provided 0.240 g of N-{4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-ylmethyl]benzyl}methanesulfonamide as white granular crystals, mp 228.0–229.0° C.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous fraction was extracted with 95:5 chloroform/methanol
  3. washwashed sequentially with water and saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting solid was purified by flash column chromatography with a gradient of CMA (2%–10%) in chloroform as the eluent
  8. customA final recrystallization from 2-propanol

Sources & evidence

ORD record
ord-eb0c87782d154fc1a5d50dcca884829e
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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