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

HRID 1675089Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=2)[N:7]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1.CCN(C(C)C)C(C)C.O>CC(N(C)C)=O>[F:12][C:11]([F:14])([F:13])[C:8]1[N:6]2[N:7]=[C:2]([N:15]3[CH2:20][CH2:19][CH:18]([C:21]4[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=4)[CH2:17][CH2:16]3)[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1

Participants

Conditions

Temperature: 110 °C

Procedure

6-Chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (2 g, 8.99 mmol), methyl 4-(piperidin-4-yl)benzoate (CAS 281235-04-9, 2.168 g, 9.89 mmol) and DIPEA (3.91 mL, 22.47 mmol) were dissolved in DMA (10 mL) and sealed into a microwave tube. The mixture was heated to 110° C. for 5 minutes in the microwave reactor and cooled to room temperature. The reaction mixture was added dropwise to stirred water (30 mL), stirred for 10 minutes then the precipitate was collected by filtration, washed with ether (2×2 mL) and dried to give methyl 4-[1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]benzoate (3.32 g, 91%) as a solid.

Workup

customsealed into a microwave tube
temperaturecooled to room temperature
additionThe reaction mixture was added dropwise
filtrationthe precipitate was collected by filtration
washwashed with ether (2×2 mL)
customdried

Sources & evidence

ORD record: ord-ae1320417f30445bb86f820d269f78ad
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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