Tetrahydrofuran → HCID 58368679, compound

HRID 1192605Notes

Reaction equation

HRID 1192605 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([N:15]2[CH2:20][CH2:19][CH:18]([F:21])[CH2:17][CH2:16]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+].O1CCCC1>CO.C(#N)C>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:28])[CH3:13])[C:9]([N:15]2[CH2:20][CH2:19][CH:18]([F:21])[CH2:17][CH2:16]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368540HCID 58368540, compound

Product 1

HCID 58368679HCID 58368679, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-[5-chloro-8-(4-fluoropiperidin-1-yl)quinolin-7-yl]ethanone (0.0364 g, 0.119 mmol) and ammonium acetate (0.0915 g, 1.19 mmol) in methanol (1.0 mL) and acetonitrile (1.0 mL) was heated at 65° C. in a sealed tube for 1 hour. After cooling to room temperature, to the resulting mixture was added 1.0 M sodium cyanoborohydride in tetrahydrofuran (0.297 mL, 0.297 mmol). 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 C16H20ClFN3 (M+H)+: m/z=308.1; Found: 308.1.

Workup

  1. temperatureAfter cooling to room temperature, to the resulting mixture
  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-bacf44fa8cfe4f5eae79896eb1006cca
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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