Sodium Carbonate → HCID 6918654, compound

HRID 2415121Notes

Reaction equation

HRID 2415121 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=3)[CH2:11][CH2:10][N:9]=2)=[CH:4][C:3]=1[O:19][CH3:20].C(=O)([O-])[O-].[Na+].[Na+].[F:27][C:28]([F:41])([F:40])[O:29][C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>O1CCOCC1>[F:41][C:28]([F:27])([F:40])[O:29][C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[C:17]4[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=4)[CH2:11][CH2:10][N:9]=3)=[CH:4][C:3]=2[O:19][CH3:20])(=[O:38])=[O:37])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 523102p-(Trifluoromethoxy)benzenesulphonyl chlorideHCID 22640493HCID 22640493, compound

Product 1

HCID 6918654HCID 6918654, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

28.7 mg of 1-(4-amino-3-methoxyphenyl)-7-chloro-3,4-dihydroisoquinoline are dissolved in 400 μl of dioxane, and 300 μl of a 0.33 molar solution of sodium carbonate are then added. 480 μl of a 0.25 molar solution of 4-trifluoromethoxybenzenesulfonyl chloride in dioxane are added to this mixture. The whole is stirred at RT for 16 h and the reaction mixture is loaded, at neutral pH, onto a cartridge containing 400 mg of diatomaceous earth and 300 mg of alumina. The product is eluted with 12 ml of dichloromethane. The eluate is concentrated and the residue is purified by flash chromatography on silica gel. 34 mg of the title compound are obtained.

Workup

  1. additioncontaining 400 mg of diatomaceous earth and 300 mg of alumina
  2. washThe product is eluted with 12 ml of dichloromethane
  3. concentrationThe eluate is concentrated
  4. customthe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-bb30110616ea4dc28f46740cc4acb288
Source dataset
uspto-grants-2004_11
Patent number
US06818651B2

Reaction notes

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