4-Toluenesulfonyl chloride → HCID 58833637, compound

HRID 2203618Notes

Reaction equation

HRID 2203618 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:30][C:31]([OH:34])([CH3:33])[CH3:32])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([O:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:12][C:11]=3[N+:10]([O-])=[CH:9][C:8]=2[N:29]=1)[CH3:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:47]>ClCCl>[NH2:47][C:9]1[C:8]2[N:29]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:6]([CH2:30][C:31]([OH:34])([CH3:33])[CH3:32])[C:7]=2[C:16]2[CH:15]=[CH:14][C:13]([O:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:12][C:11]=2[N:10]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 68975745HCID 68975745, compound

Product 1

HCID 58833637HCID 58833637, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-{[2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethylcarbamate (2.8 g, 5.05 mmol) was dissolved in dichloromethane (35 mL) and ammonium hydroxide (25 mL). p-Toluenesulfonyl chloride (0.962 g, 5.05 mmol) was added in one portion and the reaction was stirred for 16 hours. The layers were separated and the aqueous fraction was extracted with dichloromethane. The organics were combined and evaporated under reduced pressure. The residue was purified by chromatography on a HORIZON HPFC system (silica gel, 2-25% CMA in chloroform) to provide 1.95 g of tert-butyl 2-{[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethylcarbamate as white crystals.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous fraction was extracted with dichloromethane
  3. customevaporated under reduced pressure
  4. customThe residue was purified by chromatography on a HORIZON HPFC system (silica gel, 2-25% CMA in chloroform)

Sources & evidence

ORD record
ord-1458dd25de594dfca1b847ea2358e741
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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