Hydrochloric Acid → HCID 67024025, compound

HRID 450733Notes

Reaction equation

HRID 450733 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH2:16][CH:17]([CH2:23][NH:24][C:25](=O)[CH2:26][CH3:27])[CH2:18]3)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Cl>C1COCC1.C(OCC)(=O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH2:16][CH:17]([CH2:23][NH:24][CH2:25][CH2:26][CH3:27])[CH2:18]3)(=[O:11])=[O:12])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 67023968HCID 67023968, compound

Product 1

HCID 67024025HCID 67024025, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[4-(4-Isopropyl-benzenesulfonylamino)-indan-2-ylmethyl]propionamide (0.30 g, 0.75 mmol) was dissolved in 10 mL of THF and 2.5 mL (26.1 mmol) of a borane-THF complex was introduced dropwise. The resulting mixture was stirred at reflux for 1 h. The solution was cooled, 3 mL of 2 N HCl was added slowly, and the mixture was stirred at reflux for 2 h. The cooled solution was quenched with water, then NaOH (2N) and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered, and the filtrate was evaporated in vacuo to give product as a white solid which was further purified by column chromatography using (dichloromethane-MeOH, 7-12%) to give an oil. The oil was dissolved in ethyl acetate and HCl (4M, dioxane) was added to give the product as a white solid (140 mg, 43%).

Workup

  1. addition2.5 mL (26.1 mmol) of a borane-THF complex was introduced dropwise
  2. temperatureat reflux for 1 h
  3. temperatureThe solution was cooled
  4. stirringthe mixture was stirred
  5. temperatureat reflux for 2 h
  6. customThe cooled solution was quenched with water
  7. extractionNaOH (2N) and extracted with ethyl acetate
  8. dry with materialThe organic phase was dried over MgSO4
  9. filtrationfiltered
  10. customthe filtrate was evaporated in vacuo
  11. customto give product as a white solid which
  12. customwas further purified by column chromatography
  13. customto give an oil

Sources & evidence

ORD record
ord-343ca32137554b679e1e8f22a045307d
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Reaction notes

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