Ammonium Acetate → HCID 58368587, compound

HRID 1192585Notes

Reaction equation

HRID 1192585 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11]3[C:12]([C:22](=O)[CH3:23])=[CH:13][C:14]([F:21])=[C:15]4[C:20]=3[N:19]=[CH:18][CH:17]=[CH:16]4)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:31].[Na+]>CO.C(#N)C>[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11]3[C:12]([CH:22]([NH2:31])[CH3:23])=[CH:13][C:14]([F:21])=[C:15]4[C:20]=3[N:19]=[CH:18][CH:17]=[CH:16]4)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368529HCID 58368529, compound

Product 1

HCID 58368587HCID 58368587, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-[8-(4-cyclobutylpiperazin-1-yl)-5-fluoroquinolin-7-yl]ethanone (16 mg, 0.049 mmol) and ammonium acetate (37.7 mg, 0.489 mmol) in methanol (0.27 mL) and acetonitrile (0.28 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling to room temperature, sodium cyanoborohydride (6 mg, 0.01 mmol) was added. The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature and quenched with sat. sodium bicarbonate, extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The residue was used directly in the next step. LCMS calculated for C19H26FN4 (M+H)+: m/z=329.2; Found: 329.2.

Workup

  1. temperatureAfter cooling to room temperature
  2. temperatureThe reaction was heated at 65° C. for another 4 hours
  3. temperaturecooled to room temperature
  4. customquenched with sat. sodium bicarbonate
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-51e2841bd8994bbf9b44dec66a6b9299
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

Loading…