2,5-Dichlorobenzoic acid → 6-[4-(2,5-DICHLOROBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (3-METHYLBUTYL)AMIDE

HRID 2356478Notes

Reaction equation

HRID 2356478 reaction equation
[CH3:1][CH:2]([CH3:20])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:12][CH:13]=1)=[O:7].[Cl:21][C:22]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:23]=1[C:24](O)=[O:25].N12CCCN=C1CCCCC2.CN(C)CCCN=C=NCC>CN(C=O)C.CCOC(C)=O>[CH3:1][CH:2]([CH3:20])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:24](=[O:25])[C:23]3[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:22]=3[Cl:21])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1)=[O:7]

Participants

7

Reactant 4

HCID 57842,5-Dichlorobenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 668493226-Piperazin-1-yl-pyridazin-3-carboxylic acid (3-methylbutyl)amide

Product 1

HCID 865972176-[4-(2,5-DICHLOROBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (3-METHYLBUTYL)AMIDEYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-piperazin-1-yl-pyridazine-3-carboxylic acid (3-methylbutyl)amide (0.255 mmol), 2,5-dichlorobenzoic acid (0.31 mmol), 1,8-diazabicylco[5.4.0]undec-7-ene (0.51 mmol) and 1-hydroxybenozotriazole hydrate (0.31 mmol) in DMF (2 mL) was stirred at ambient temperature for 15 min. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (0.31 mmol) was then added. The mixture was stirred at ambient temperature overnight, and then diluted with EtOAc (50 mL) and washed with aqueous saturated NaHCO3 (2×20 mL) and brine (2×20 mL). The organic extract was dried over anhydrous Na SO4, concentrated, and purified by flash chromatography to give the title compound as a white solid (102 mg, 89% yield). 1H NMR (500 MHz, CDCl3) δ 8.07, 7.85, 7.32-7.40, 7.01, 4.01-4.08, 3.77-3.93, 3.35-3.55, 1.65-1.75, 1.52, 0.94. MS (ES+) m/z 450 (M+1).

Workup

  1. stirringThe mixture was stirred at ambient temperature overnight
  2. washwashed with aqueous saturated NaHCO3 (2×20 mL) and brine (2×20 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous Na SO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-b12eac81302d44f3aa99f92a71d6ec92
Source dataset
uspto-grants-2010_07
Patent number
US07759348B2

Reaction notes

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