Tetrahydrofuran → HCID 58368499, compound

HRID 1192675Notes

Reaction equation

HRID 1192675 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[C:19]([C:29](=O)[CH3:30])=[CH:20][C:21]([Cl:28])=[C:22]4[C:27]=3[N:26]=[CH:25][CH:24]=[CH:23]4)[CH2:14][CH2:13]2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:38].[Na+].O1CCCC1>CO.C(#N)C>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[C:19]([CH:29]([NH2:38])[CH3:30])=[CH:20][C:21]([Cl:28])=[C:22]4[C:27]=3[N:26]=[CH:25][CH:24]=[CH:23]4)[CH2:14][CH2:13]2)=[O:11])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368596HCID 58368596, compound

Product 1

HCID 58368499HCID 58368499, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-(8-{4-[(1-acetylpiperidin-4-yl)carbonyl]piperazin-1-yl}-5-chloroquinolin-7-yl)ethanone (0.030 g, 0.068 mmol) and ammonium acetate (0.0522 g, 0.677 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, to the resulting mixture was added 1.0 M sodium cyanoborohydride in tetrahydrofuran (0.17 mL, 0.17 mmol). The reaction was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with sat. NaHCO3 solution, extracted with dichloromethane, dried over MgSO4 and concentrated to give the desired product. LCMS calculated for C23H31ClN5O2 (M+H)+: m/z=444.2; Found: 444.2.

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 materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f95518ff68254068a80209a794e1b485
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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