Diisopropylethylamine → 6-(3-Phenylpiperidin-1-yl)-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine

HRID 1675109Notes

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

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (49 mg, 0.22 mmol) in EtOH (1.0 mL) was added to a mixture of 3-phenylpiperidine (53 mg, 0.33 mmol) and DIPEA (57 μL, 0.33 mmol) in EtOH (1.0 mL). The reaction mixture was heated to 70° C. overnight and the crude product was purified by preparative LCMS (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 5% ammonia) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to give 6-(3-phenylpiperidin-1-yl)-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (46 mg, 61%).

Workup

customthe crude product was purified by preparative LCMS (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length)
additionFractions containing the desired compound
customwere evaporated to dryness

Sources & evidence

ORD record: ord-e5a3381e7f8f4652bbdfe336bdcda945
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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