Ammonium Acetate → HCID 86666776, compound

HRID 510846Notes

Reaction equation

HRID 510846 reaction equation
[C:1]([N:4]([C:8]1[C:13]([CH3:14])=[C:12]([Cl:15])[CH:11]=[C:10]([C:16](=O)[CH3:17])[C:9]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)C(=O)C)(=[O:3])[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:32].[Na+]>CO.C(#N)C>[NH2:32][CH:16]([C:10]1[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[C:8]([NH:4][C:1](=[O:3])[CH3:2])[C:13]([CH3:14])=[C:12]([Cl:15])[CH:11]=1)[CH3:17]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 86666777HCID 86666777, compound

Product 1

HCID 86666776HCID 86666776, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of N-acetyl-N-(6-acetyl-4-chloro-3′-fluoro-3-methylbiphenyl-2-yl)acetamide (57 mg, 0.16 mmol), ammonium acetate (120 mg, 1.6 mmol) and sodium cyanoborohydride (20 mg, 0.32 mmol) in methanol (0.6 mL) and acetonitrile (0.6 mL) was heated at 65° C. overnight in a sealed tube. The mixture was then cooled to room temperature and quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The crude product was used directly in next step. LCMS calculated for C17H19ClFN2O (M+H)+: m/z=321.1. found: 321.0.

Workup

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

Sources & evidence

ORD record
ord-56e734bb29f64cc6ac4cda5004be83e9
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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