1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-[4-(2-TRIFLUOROMETHYLBENZYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (3-METHYLBUTYL)AMIDE

HRID 2056530Notes

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].[F:21][C:22]([F:32])([F:31])[C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25]Cl.N12CCCN=C1CCCCC2>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]([CH2:25][C:24]3[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=3[C:22]([F:21])([F:31])[F:32])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1)=[O:7]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 6-piperazin-1-yl-pyridazine-3-carboxylic acid (3-methylbutyl)amide (0.255 mmol), 2-trifluoromethylbenzyl chloride (0.255 mmol), and 1,8-diazabicylco[5.4.0]undec-7-ene (0.77 mmol) was stirred and heated at 60° C. overnight. The reaction mixture was ten diluted with EtOAc (100 mL) and washed with aqueous saturated NaHCO3 (2×20 mL) and brine (2×20 mL). The organic layer was dried over anhydrous Na2SO4, concentrated, and purified by flash chromatography to give the title compound as a white solid (80 mg, 72% yield). 1H NMR (500 MHz, CDCl3) δ 8.00, 7.86, 7.82, 7.65, 7.55, 7.37, 6.95, 3.74-3.79, 3.73, 3.46-3.52, 2.62, 1.65-1.76, 1.52, 0.94. MS (ES+) m/z 436 (M+1).

Workup

washwashed with aqueous saturated NaHCO3 (2×20 mL) and brine (2×20 mL)
dry with materialThe organic layer was dried over anhydrous Na2SO4
concentrationconcentrated
custompurified by flash chromatography

Sources & evidence

ORD record: ord-75a918b936504b729a8aef1ac515de8b
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07335658B2

Reaction notes

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