Tetrahydrofuran → HCID 58368594, compound

HRID 1192637Notes

Reaction equation

HRID 1192637 reaction equation
[C:1]([C:4]1[C:13]([N:14]2[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:23])[CH2:21][CH3:22])[CH2:15]2)=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[C:6]([Cl:24])[CH:5]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:31].[Na+].O1CCCC1>CO.C(#N)C>[NH2:31][CH:1]([C:4]1[C:13]([N:14]2[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:23])[CH2:21][CH3:22])[CH2:15]2)=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[C:6]([Cl:24])[CH:5]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368575HCID 58368575, compound

Product 1

HCID 58368594HCID 58368594, 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]propanamide (0.011 g, 0.032 mmol) and ammonium acetate (0.0245 g, 0.318 mmol) in methanol (0.15 mL) and acetonitrile (0.15 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 (0.080 mL, 0.080 mmol). The reaction was heated at 65° C. overnight, then cooled to room temperature, quenched with sat. NaHCO3 solution and extracted with dichloromethane. The combined organic phase were dried over MgSO4 and concentrated to give the desired product. LCMS calculated for C18H24ClN4O (M+H)+: m/z=347.2; Found: 347.1.

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. customquenched with sat. NaHCO3 solution
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic phase were dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-830a6cddd3e9428faf84ff80cc391523
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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