Water → 2-cyclopropylmethyl-6-(2,3-dihydro-1-benzofuran-5-yl)-4-(1-piperazinyl)methyl-2H-pyridazin-3-one

HRID 2249412Notes

Reaction equation

HRID 2249412 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[C:16](=[O:34])[N:17]([CH2:30][CH:31]3[CH2:33][CH2:32]3)[N:18]=[C:19]([C:21]3[CH:22]=[CH:23][C:24]4[O:28][CH2:27][CH2:26][C:25]=4[CH:29]=3)[CH:20]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.O.C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O>[CH:31]1([CH2:30][N:17]2[C:16](=[O:34])[C:15]([CH2:14][N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:20][C:19]([C:21]3[CH:22]=[CH:23][C:24]4[O:28][CH2:27][CH2:26][C:25]=4[CH:29]=3)=[N:18]2)[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 230941054-(4-tert-butoxycarbonyl-1-piperazinyl)methyl-2-cyclopropylmethyl-6-(2,3-dihydro-1-benzofuran-5-yl)-2H-pyridazin-3-one

Product 1

HCID 230941062-cyclopropylmethyl-6-(2,3-dihydro-1-benzofuran-5-yl)-4-(1-piperazinyl)methyl-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-(4-tert-Butoxycarbonyl-1-piperazinyl)methyl-2-cyclopropylmethyl-6-(2,3-dihydro-1-benzofuran-5-yl)-2H-pyridazin-3-one (121 mg, 0.26 mmol) was dissolved in trifluoroacetic acid (1.1 mL) under cooling with ice-water, and the solution was stirred for 15 minutes at the same temperature. Water (10 mL) was added to the reaction mixture, and the resultant mixture was made alkaline with potassium carbonate, followed by extraction with chloroform. The organic layer was washed with saturated brine (20 mL) and dried over sodium sulfate anhydrate, and the solvent was removed under reduced pressure, to thereby yield 83 mg (87.4%) of the title compound as a yellow oil.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with saturated brine (20 mL)
  3. dry with materialdried over sodium sulfate anhydrate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-df24c27cd30943f3a541320e6b2dba8a
Source dataset
uspto-grants-2008_01
Patent number
US07314877B2

Reaction notes

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