Tetrahydrofuran → HCID 58368524, compound

HRID 1192568Notes

Reaction equation

HRID 1192568 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([C:13](=O)[CH3:14])[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:29].[Na+].O1CCCC1>CO.C(#N)C>[CH2:1]([C:3]1[CH:12]=[C:11]([CH:13]([NH2:29])[CH3:14])[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2)[CH3:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368595HCID 58368595, compound

Product 1

HCID 58368524HCID 58368524, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-[5-ethyl-8-(3-fluorophenyl)quinolin-7-yl]ethanone (6.1 mg, 0.021 mmol) and ammonium acetate (0.017 g, 0.22 mmol) in methanol (0.3 mL) and acetonitrile (0.3 mL) was heated at 65° C. in a sealed tube for 1 hour. After cooling to room temperature, 1.0 M sodium cyanoborohydride in tetrahydrofuran (0.052 mL, 0.052 mmol) was added to the mixture. The reaction was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with sat. NaHCO3 solution and extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to give the desired product. LCMS calculated for C19H20FN2 (M+H)+: m/z=295.2; Found: 295.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. temperatureThe reaction was heated at 65° C. overnight
  3. temperatureThe mixture was cooled to room temperature
  4. customquenched with sat. NaHCO3 solution
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5b4cd867a0bc44d6b2389ded2e8a23ef
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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