Hydrazine hydrate (1:1) → HCID 58181225, compound

HRID 1465507Notes

Reaction equation

HRID 1465507 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]([CH2:23][CH2:24][CH2:25][OH:26])[S:21][CH:22]=3)=[N:14][CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:27]([N:34]1C=CN=C1)(N1C=CN=C1)=[O:28].O1CCCC1.[NH2:44]N.O.NN>O1CCCC1>[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]([CH2:23][CH2:24][CH2:25][O:26][C:27]([NH:34][NH2:44])=[O:28])[S:21][CH:22]=3)=[N:14][CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 682631,1'-CarbonyldiimidazoleHCID 58181239HCID 58181239, compoundHCID 67030329HCID 67030329, compound

Product 1

HCID 58181225HCID 58181225, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}thiophen-2-yl)propan-1-ol (150.0 mg, 0.402 mmol) in anhydrous tetrahydrofuran (3 ml) was added 1,1′-carbonyldiimidazole (84.7 mg, 0.522 mmol), and the mixture was stirred at room temperature for 2 hrs. 1M Hydrazine tetrahydrofuran solution (1.21 ml, 1.21 mmol) was added, and the mixture was stirred at room temperature for 2 hrs. Since the reaction did not proceed, hydrazine monohydrate (26.1 mg, 0.522 mmol) was added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by aminopropylated silica gel column chromatography (5%-2-propanol-dichloromethane mixture) and aminopropylated silica gel column chromatography (2%-methanol-dichloromethane mixture) to give the title compound (148.8 mg, yield 85.9%) as a colorless syrup.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hrs
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by aminopropylated silica gel column chromatography (5%-2-propanol-dichloromethane mixture) and aminopropylated silica gel column chromatography (2%-methanol-dichloromethane mixture)

Sources & evidence

ORD record
ord-04c1036c1e854e6392634e83e490949d
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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