Diisopropylethylamine → Ethyl 3-[1-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl]benzoate

HRID 1675129Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:3][CH2:2]1.Cl[C:19]1[CH:20]=[CH:21][C:22]2[N:23]([C:25]([C:28]([F:31])([F:30])[F:29])=[N:26][N:27]=2)[N:24]=1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[F:30][C:28]([F:29])([F:31])[C:25]1[N:23]2[N:24]=[C:19]([N:1]3[CH2:6][CH2:5][CH:4]([C:7]4[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=4)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:3][CH2:2]3)[CH:20]=[CH:21][C:22]2=[N:27][N:26]=1

Participants

Conditions

Temperature: 125 °C

Procedure

Ethyl 3-(piperidin-4-yl)benzoate (1.195 g, 5.12 mmol) was added to 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (1 g, 4.49 mmol) and DIPEA (1.174 mL, 6.74 mmol) in DMA (10 mL). The resulting solution was stirred at 125° C. for 2 hours. The reaction mixture was evaporated to dryness, redissolved in DCM and purified by flash silica chromatography, eluting with 50% EtOAc in isohexane. Pure fractions were evaporated to dryness to give a beige solid, which was triturated with ether to give ethyl 3-[1-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl]benzoate (0.805 g, 42.7%) as a solid.

Workup

customThe reaction mixture was evaporated to dryness
dissolutionredissolved in DCM
custompurified by flash silica chromatography
washeluting with 50% EtOAc in isohexane
customPure fractions were evaporated to dryness
customto give a beige solid, which
customwas triturated with ether

Sources & evidence

ORD record: ord-1c9a7b2d438947e587240e0d41c477e6
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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