Tetrahydrofuran → HCID 58368479, compound

HRID 1192640Notes

Reaction equation

HRID 1192640 reaction equation
[C:1]([C:4]1[C:13]([N:14]2[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[CH2:15]2)=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[C:6]([Cl:25])[CH:5]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:32].[Na+].O1CCCC1>CO.C(#N)C>[NH2:32][CH:1]([C:4]1[C:13]([N:14]2[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[CH2:15]2)=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[C:6]([Cl:25])[CH:5]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368639HCID 58368639, compound

Product 1

HCID 58368479HCID 58368479, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of N-[(3S)-1-(7-acetyl-5-chloroquinolin-8-yl)pyrrolidin-3-yl]-2-methylpropanamide (0.031 g, 0.086 mmol) and ammonium acetate (0.066 g, 0.86 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 (0.21 mL, 0.21 mmol). The reaction was heated at 65° C. overnight and then cooled to room temperature. The mixture was quenched with sat. NaHCO3 solution, extracted with dichloromethane, dried over MgSO4 and concentrated to give the desired product. LCMS calculated for C19H26ClN4O (M+H)+: m/z=361.2; Found: 361.2.

Workup

  1. temperatureAfter cooling to room temperature, to the resulting mixture
  2. temperatureThe reaction was heated at 65° C. overnight
  3. temperaturecooled to room temperature
  4. customThe mixture was quenched with sat. NaHCO3 solution
  5. extractionextracted with dichloromethane
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-269566179b154af797eeecfedd60beac
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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