4-METHYL-2-({6-[4-(2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]-PYRIDAZINE-3-CARBONYL}AMINO)PENTANOIC Acid Methyl Ester → 4-Methyl-2-({6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carbonyl}amino)pentanoic acid

HRID 2056596Notes

Reaction equation

HRID 2056596 reaction equation
[H-].[OH-].[Li+].C[O:5][C:6](=[O:39])[CH:7]([NH:12][C:13]([C:15]1[N:16]=[N:17][C:18]([N:21]2[CH2:26][CH2:25][N:24]([C:27](=[O:38])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:37])([F:36])[F:35])[CH2:23][CH2:22]2)=[CH:19][CH:20]=1)=[O:14])[CH2:8][CH:9]([CH3:11])[CH3:10]>O1CCCC1.O>[CH3:10][CH:9]([CH3:11])[CH2:8][CH:7]([NH:12][C:13]([C:15]1[N:16]=[N:17][C:18]([N:21]2[CH2:22][CH2:23][N:24]([C:27](=[O:38])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:37])([F:36])[F:35])[CH2:25][CH2:26]2)=[CH:19][CH:20]=1)=[O:14])[C:6]([OH:39])=[O:5]

Participants

5

Reactant 2

HCID 160357644-METHYL-2-({6-[4-(2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]-PYRIDAZINE-3-CARBONYL}AMINO)PENTANOIC Acid Methyl EsterHCID 86597229HCID 86597229, compound

Product 1

HCID 160358754-Methyl-2-({6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carbonyl}amino)pentanoic acidYield 74.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydride (25 mg, 0.595 mmol) was added to a solution of 4-methyl-2-({6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carbonyl}-amino)pentanoic acid methyl ester (130 mg, 0.256 mmol) in tetrahydrofuran (3 mL) and water (1.5 mL), the reaction mixture was stirred at ambient temperature for 3 hours, THF was removed by evaporation, the residue was adjusted with 5% citric acid to pH about 6, and diluted with ethyl acetate, washed with water and brine, dried (Na2SO4) and concentrated to afford 4-methyl-2-({6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carbonyl}amino)pentanoic acid (94 mg, 74%). 1H NMR (400 MHz, CDCl3) δ 8.17, 8.02, 7.78, 7.66-7.53, 7.38, 6.99, 6.72, 4.88-4.73, 4.25-3.60, 3.44-3.21, 1.79-1.06, 1.33-1.19, 1.03, 0.99.

Workup

  1. customTHF was removed by evaporation
  2. additiondiluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-db8b554bf7c842f8abee7ecdd57b08c1
Source dataset
uspto-grants-2008_02
Patent number
US07335658B2

Reaction notes

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