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Water → HCID 11340491, compound

HRID 2356580
Notes
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Reaction equation

HRID 2356580 reaction equation
[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12]([N:15]3[CH2:20][CH:19]([CH3:21])[NH:18][CH:17]([CH3:22])[CH2:16]3)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[F:32][C:33]([F:44])([F:43])[C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36](Cl)=[O:37].O>ClCCl>[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12]([N:15]3[CH2:20][CH:19]([CH3:21])[N:18]([C:36](=[O:37])[C:35]4[CH:39]=[CH:40][CH:41]=[CH:42][C:34]=4[C:33]([F:32])([F:43])[F:44])[CH:17]([CH3:22])[CH2:16]3)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 66849584N-(2-Cyclopropylethyl)-6-(3,5-dimethyl-1-piperazinyl)-3-pyridazinecarboxamide

Product 1

HCID 11340491HCID 11340491, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 6-(3,5-dimethylpiperazin-1-yl)pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (0.40 g, 1.33 mmol) in dichloromethane (15 mL) was added diisopropyl ethylamine (0.34 g, 0.46 mL, 2.66 mmol) followed by 2-trifluoromethylbenzoyl chloride (0.31 g, 0.22 mL, 1.46 mmol) at ambient temperature. The reaction solution was stirred for 16 hours and poured into cold water (10 mL). The organic layer was extracted with dichloromethane (50 mL) and washed with saturated solution of NaHCO3 (2×10 mL) and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo. The crude material was purified by column chromatography eluting with ethyl acetate (100%) to obtain 0.18 g of colorless solid (28% yield). 1H NMR (300 MHz, CDCl3) δ 8.03-7.91, 7.70, 7.63-7.49, 7.32, 6.99-6.95, 5.00, 4.39-4.22, 3.64, 3.55-3.47, 3.39-3.17, 1.51-1.38, 1.24-1.14, 0.76-0.67, 0.42, 0.05. 13C NMR (75 MHz, CDCl3) δ 168.0, 163.0, 160.9, 144.9, 132.3, 131.9, 129.4, 129.3, 127.2, 127.0, 126.8, 111.5, 50.4, 49.1, 48.7, 48.5, 48.2, 45.5, 45.3, 39.6, 34.6, 20.2, 19.5, 8.6, 4.2.

Workup

  1. extractionThe organic layer was extracted with dichloromethane (50 mL)
  2. washwashed with saturated solution of NaHCO3 (2×10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe crude material was purified by column chromatography
  7. washeluting with ethyl acetate (100%)

Sources & evidence

ORD record
ord-51fd4232decd43e99f0196b8e65242d5
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07759348B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes