Potassium Hydroxide → HCID 71255433, compound

HRID 540269Notes

Reaction equation

HRID 540269 reaction equation
[O:1]=[S:2]1(=[O:28])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[CH:22]=[C:21]([CH2:23][CH2:24][C:25]#[N:26])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:27])[CH:19]=3)[N:14]=2)[CH2:4][CH2:3]1.[OH-:29].[K+]>C(O)(C)(C)C.O>[O:28]=[S:2]1(=[O:1])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[CH:22]=[C:21]([CH2:23][CH2:24][C:25]([NH2:26])=[O:29])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:27])[CH:19]=3)[N:14]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 71255457HCID 71255457, compound

Product 1

HCID 71255433HCID 71255433, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 3-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]-propionitrile (150 mg, 0.38 mmol), and powdered potassium hydroxide (172 mg, 3.07 mmol) in tert-butanol (8 mL) was heated with stirring under reflux for 1.5 hours. After being cooled to room temperature, the reaction mixture was diluted with water (15 mL) and extracted with ethyl acetate (15 mL×3). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column (eluting with 5% methanol in dichloromethane) to afford 125 mg of the product as a white solid.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. extractionextracted with ethyl acetate (15 mL×3)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column (eluting with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-72f141dd31d94a8fb8e9c5d3a4684dfd
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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