Hydrochloric Acid → 6-[4-(2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid

HRID 2354631Notes

Reaction equation

HRID 2354631 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[N:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:26])[F:25])[CH2:13][CH2:12]2)=[CH:9][CH:10]=1)=[O:4].O.[OH-].[Li+].Cl>O1CCCC1.O>[F:27][C:24]([F:25])([F:26])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:17]([N:14]1[CH2:15][CH2:16][N:11]([C:8]2[N:7]=[N:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=2)[CH2:12][CH2:13]1)=[O:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 668495266-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid methyl ester

Product 1

HCID 454873706-[4-(2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC AcidYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid methyl ester (4.436 g, 11.25 mmol) in tetrahydrofuran (50 mL) and water (25 mL) was added lithium hydroxide monohydrate (2.30 g, 54.81 mmol). The reaction mixture was stirred at ambient temperature for 23 h and the pH of the solution was adjusted to ˜3 with concentrate hydrochloric acid (5.3 mL) at 0° C. The mixture was concentrated. Ethyl acetate (100 mL) was added to the residue and the product was precipited. The solid was collected by filtration, washed with ethyl acetate and dried in vacuo to afford the title compound (3.60 g). The aqueous layer was extracted with ethyl acetate, dried over Na2SO4 and concentrated to give the second portion of title compound (0.463 g). The total amount of product was 4.063 g (95% yield).

Workup

  1. concentrationThe mixture was concentrated
  2. additionEthyl acetate (100 mL) was added to the residue
  3. filtrationThe solid was collected by filtration
  4. washwashed with ethyl acetate
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a9fce6dc474f40b3b7ef2e3aa3f1aa7b
Source dataset
uspto-grants-2010_07
Patent number
US07754711B2

Reaction notes

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