Water → HCID 18668765, compound

HRID 1058635Notes

Reaction equation

HRID 1058635 reaction equation
FC(F)(F)C(O)=O.[O:8]([C:15]1[C:24]2[N:25]=[CH:26][N:27]([CH2:28][CH2:29][CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:23]=2[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.O.C(OCC)(=O)C.[CH3:50][S:51](Cl)(=[O:53])=[O:52]>C(Cl)Cl>[CH3:50][S:51]([N:33]1[CH2:34][CH2:35][CH:30]([CH2:29][CH2:28][N:27]2[C:23]3[C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[N:16]=[C:15]([O:8][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:24]=3[N:25]=[CH:26]2)[CH2:31][CH2:32]1)(=[O:53])=[O:52]

Participants

7

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 18668750HCID 18668750, compound

Product 1

HCID 18668765HCID 18668765, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.00 g of 4-phenoxy-1-[2-(4-piperidyl)ethyl]-1H-imidazo-[4,5-c]quinoline trifluoroacetate and 0.57 ml of triethylamine in 10 ml of methylene chloride, 0.16 ml of methanesulfonyl chloride was added dropwise at room temperature, and the mixture was stirred for 1.5 hours. The reaction mixture was added with water, and extracted with methylene chloride. The extract was washed with water, and dried, and then the solvent was evaporated to give a colorless liquid. The resulting colorless liquid was solidified with ethyl acetate, and the solid was washed with diethyl ether to give 0.80 g of colorless crystals. Recrystallization from a mixture of methylene chloride and ethyl acetate gave colorless crystals having the melting point of from 173.5 to 176° C.

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was evaporated
  5. customto give a colorless liquid
  6. washthe solid was washed with diethyl ether

Sources & evidence

ORD record
ord-a22195d2b0514548994bb7c868287fb6
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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