Ammonium Acetate → HCID 86666792, compound

HRID 510861Notes

Reaction equation

HRID 510861 reaction equation
[C:1]([C:4]1[C:5]([O:18][CH3:19])=[C:6]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[C:7]([CH3:11])=[C:8]([Cl:10])[CH:9]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:26].[Na+]>CO.C(#N)C>[NH2:26][CH:1]([C:4]1[C:5]([O:18][CH3:19])=[C:6]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[C:7]([CH3:11])=[C:8]([Cl:10])[CH:9]=1)[CH3:2]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 86666791HCID 86666791, compound

Product 1

HCID 86666792HCID 86666792, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-(3-acetyl-5-chloro-2-methoxy-6-methylphenyl)pyrrolidin-2-one (20 mg, 0.07 mmol), ammonium acetate (55 mg, 0.71 mmol) and sodium cyanoborohydride (9.0 mg, 0.14 mmol) in methanol (0.2 mL) and acetonitrile (0.2 mL) was heated at 65° C. overnight in a sealed tube. The mixture was cooled to room temperature, quenched with saturated sodium bicarbonate and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The crude product was used directly in next step (11 mg, 50%). LCMS calculated for C14H20ClN2O2 (M+H)+: m/z=283.1. found: 283.1.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with saturated sodium bicarbonate
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-7279ad4d98f24cf59a850cc64bfd9290
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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