Potassium Hydroxide → HCID 59369329, compound

HRID 1689828Notes

Reaction equation

HRID 1689828 reaction equation
[OH-].[K+].[CH:3]1([C:6]2[O:10][N:9]=[C:8]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[C:7]=2[CH2:19][O:20][CH:21]2[CH2:27][CH2:26][CH2:25][N:24]([C:28]3[CH:40]=[CH:39][C:31]4[C:32]([C:35]([O:37]C)=[O:36])=[N:33][S:34][C:30]=4[CH:29]=3)[CH2:23][CH2:22]2)[CH2:5][CH2:4]1>C(O)C.O1CCCC1>[CH:3]1([C:6]2[O:10][N:9]=[C:8]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[C:7]=2[CH2:19][O:20][CH:21]2[CH2:27][CH2:26][CH2:25][N:24]([C:28]3[CH:40]=[CH:39][C:31]4[C:32]([C:35]([OH:37])=[O:36])=[N:33][S:34][C:30]=4[CH:29]=3)[CH2:23][CH2:22]2)[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59369338HCID 59369338, compound

Product 1

HCID 59369329HCID 59369329, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Potassium hydroxide (0.118 g, 2.10 mmol) is added to a solution of methyl 6-(4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)azepan-1-yl)benzo[d]isothiazole-3-carboxylate (0.30 g, 0.52 mmol) in ethanol (2 ml) and tetrahydrofuran (6 mL). The mixture is stirred at 60° C. for 24 h and concentrated in vacuo. The residue is dissolved in water (8 ml), acidified to pH˜5 with 1 N HCl and extracted with dichloromethane (2×10 ml). The organic extracts are dried over sodium sulfate and the solvent is evaporated in vacuo to give 0.15 g (51.0%) of the title compound as an off white solid. ES/MS m/z 558.06 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in water (8 ml)
  3. extractionextracted with dichloromethane (2×10 ml)
  4. dry with materialThe organic extracts are dried over sodium sulfate
  5. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-7657f187506c471483d9091f19b5d0bb
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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