Tetrahydrofuran → HCID 58368680, compound

HRID 1192607Notes

Reaction equation

HRID 1192607 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][CH2:18][CH:17]([CH2:21][OH:22])[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:29].[Na+].O1CCCC1>CO.C(#N)C>[NH2:29][CH:12]([C:10]1[C:9]([N:15]2[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][OH:22])[CH2:16]2)=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([Cl:1])[CH:11]=1)[CH3:13]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368509HCID 58368509, compound

Product 1

HCID 58368680HCID 58368680, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-{5-chloro-8-[3-(hydroxymethyl)piperidin-1-yl]quinolin-7-yl}ethanone (0.0235 g, 0.0737 mmol) and ammonium acetate (0.0568 g, 0.737 mmol) in methanol (0.5 mL) and acetonitrile (0.5 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 (0.184 mL, 0.184 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 C17H23ClN3O (M+H)+: m/z=320.2; Found: 320.2.

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 materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-48aeffce120c406bbf1ad979b237f7f7
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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