Water → HCID 58181320, compound

HRID 1465496Notes

Reaction equation

HRID 1465496 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]3[CH:19]=[C:20]([CH2:24][C:25](O)=[O:26])[CH:21]=[CH:22][CH:23]=3)=[N:14][CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:40]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])(=[O:43])[NH:41][NH2:42].O>CN(C)C=O.C(OCC)(=O)C>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]3[CH:19]=[C:20]([CH2:24][C:25]([NH:42][NH:41][C:40]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[O:26])[CH:21]=[CH:22][CH:23]=3)=[N:14][CH:15]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 70091tert-Butyl carbazateHCID 58181367HCID 58181367, compound

Product 1

HCID 58181320HCID 58181320, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (3-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)acetic acid (213.4 mg, 0.581 mmol) in anhydrous N,N-dimethylformamide (3 ml) was added 1,1′-carbonyldiimidazole (188.9 mg, 1.165 mmol), and the mixture was stirred at room temperature for 1.5 hrs. tert-Butyl carbazate (460.3 mg, 3.483 mmol) was added, and the mixture was stirred at room temperature for 14 hrs. Water and ethyl acetate were added to the reaction mixture, and the mixture was stirred, stood still and partitioned. The aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified 3 times by silica gel column chromatography (ethyl acetate→methanol: dichloromethane=1:15, methanol:dichloromethane=1:20, methanol:dichloromethane=1:20) to give tert-butyl 2-[(3-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)acetyl]hydrazinecarboxylate (219.4 mg, yield 78.4%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 14 hrs
  2. stirringthe mixture was stirred
  3. custompartitioned
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified 3 times by silica gel column chromatography (ethyl acetate→methanol: dichloromethane=1:15, methanol:dichloromethane=1:20, methanol:dichloromethane=1:20)

Sources & evidence

ORD record
ord-c120501bfcec4f5aa791cfb9f377b893
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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