Diisopropylethylamine → HCID 59149700, compound

HRID 1674982Notes

Reaction equation

Cl.Cl.[N:3]1([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([C:18]([F:21])([F:20])[F:19])=[N:16][N:17]=3)[N:14]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[F:31][C:32]1[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=1[CH2:34][CH2:35]Br>CN(C=O)C>[F:31][C:32]1[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=1[CH2:34][CH2:35][N:6]1[CH2:5][CH2:4][N:3]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([C:18]([F:19])([F:20])[F:21])=[N:16][N:17]=3)[N:14]=2)[CH2:8][CH2:7]1

Participants

Conditions

Temperature: 100 °C

Procedure

A stirred solution of 6-(piperazin-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine dihydrochloride (0.173 g, 0.5 mmol), DIPEA (0.300 mL, 1.75 mmol) and 2-fluorophenethyl bromide (0.084 mL, 0.60 mmol) in DMF (2 mL) was heated at 100° C. for 2.5 hours. The reaction was incomplete and further DIPEA (0.300 mL, 1.75 mmol) and 2-fluorophenethyl bromide (0.084 mL, 0.60 mmol) were added. The solution was stirred at 100° C. for a further 90 minutes. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% ammonia) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 6-[4-[2-(2-fluorophenyl)ethyl]piperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (0.131 g, 66.4%) as a crisp foam.

Workup

customThe crude product was purified by preparative HPLC (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-ba4af31bde7e4aa0b126df610db765e2
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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