6-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid (2-aminopropyl)amide → HCID 178430324, compound

HRID 499178Notes

Reaction equation

HRID 499178 reaction equation
[NH2:1][CH:2]([CH3:31])[CH2:3][NH:4][C:5]([C:7]1[N:8]=[N:9][C:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19](=[O:30])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])[CH2:15][CH2:14]2)=[CH:11][CH:12]=1)=O>O=P(Cl)(Cl)Cl>[CH3:31][CH:2]1[CH2:3][NH:4][C:5]([C:7]2[N:8]=[N:9][C:10]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])=[O:30])[CH2:15][CH2:14]3)=[CH:11][CH:12]=2)=[N:1]1

Participants

3

Reactant 1

HCID 866197506-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid (2-aminopropyl)amide

Product 1

HCID 178430324HCID 178430324, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

6-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid (2-aminopropyl)amide (0.100 g, 0.229 mmol) was refluxed in POCl3 (3 mL) for 6 hours. The mixture was cooled, concentrated and quenched with 1 N NaOH (3 mL). The brown solution was extracted with dichloromethane. The organic phase was dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to afford the title compound as thick syrup in 55% yield (0.053 g). 1H NMR (300 MHz, CDCl3) 8.10 (d, J=9.6 Hz, 1H), 7.71 (d, J=7.4 Hz, 1H), 7.65-7.50 (m, 2H), 7.34 (d, J=7.4 Hz, 1H), 6.94 (d, J=9.6 Hz, 1H), 4.25-4.12 (m, 1H), 4.10-3.60 (m, 7H), 3.41 (dd, J=7.6, 11.8 Hz, 1H), 3.30 (t, J=5.1 Hz, 2H), 1.30 (d, J=6.3 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ167.6, 160.9, 159.5, 143.2, 134.2, 134.2, 132.4, 129.5, 127.5, 127.2, 127.1, 126.9, 126.9, 126.8, 126.7, 125.4, 121.8, 112.2, 46.3, 44.5, 44.4, 41.2, 21.6. MS (ES+) m/z 419.2 (M+1).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. customquenched with 1 N NaOH (3 mL)
  4. extractionThe brown solution was extracted with dichloromethane
  5. dry with materialThe organic phase was dried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5aa0fb0da66c4a10abff015a567509df
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

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