Sodium Carbonate → 5-(4-(5-cyanopyridin-2-yl)-2-methylpiperazin-1-yl)-N'-hydroxy-5-oxopentanimidamide

HRID 874958Notes

Reaction equation

HRID 874958 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=2)[CH2:10][CH:9]1[CH3:22])=[O:7])#[N:2].Cl.[NH2:24][OH:25].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O.OC1C=CC=C2C=1N=CC=C2>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:6](=[O:7])[CH2:5][CH2:4][CH2:3][C:1](=[N:24][OH:25])[NH2:2])[CH:9]([CH3:22])[CH2:10]2)=[N:15][CH:16]=1)#[N:19]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 673254606-(4-(4-Cyanobutanoyl)-3-methylpiperazin-1-yl)nicotinonitrile

Product 1

HCID 866735335-(4-(5-cyanopyridin-2-yl)-2-methylpiperazin-1-yl)-N'-hydroxy-5-oxopentanimidamideYield 40%

Reagents, catalysts & solvents 3

HCID 19238-HydroxyquinolineCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

8-Hydroxyquinoline (14 mg) was added to a solution of 6-(4-(4-cyanobutanoyl)-3-methylpiperazin-1-yl)nicotinonitrile (0.9 g, 3.03 mmol) in ethanol (25 mL). Hydroxylamine hydrochloride (440 mg, 6.36 mmol) in water (4 mL), followed by sodium carbonate (510 mg, 4.81 mmol) in water (3 mL), were added to this solution and the reaction mixture was heated to reflux for 3 h. Ethanol was then removed under reduced pressure, and the product was extracted with EtOAc. The combined extracts were dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 5-(4-(5-cyanopyridin-2-yl)-2-methylpiperazin-1-yl)-N′-hydroxy-5-oxopentanimidamide (400 mg, crude), which was carried through without further purification. MS (ESI) m/z: Calculated for C16H22N6O2: 330.18. found: 331.1 (M+H)+

Workup

  1. additionwere added to this solution
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 3 h
  4. customEthanol was then removed under reduced pressure
  5. extractionthe product was extracted with EtOAc
  6. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c1c87d685a441aba8a3b283749dac37
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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