Triethylamine → 2-(4-{1-[3-(Trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenoxy)ethyl methanesulfonate

HRID 2381141Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]([F:34])([F:33])[C:8]1[N:12]2[N:13]=[C:14]([N:17]3[CH2:22][CH2:21][CH:20]([C:23]4[CH:32]=[CH:31][C:26]([O:27][CH2:28][CH2:29][OH:30])=[CH:25][CH:24]=4)[CH2:19][CH2:18]3)[CH2:15][CH2:16][C:11]2=[N:10][N:9]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:30][CH2:29][CH2:28][O:27][C:26]1[CH:31]=[CH:32][C:23]([CH:20]2[CH2:21][CH2:22][N:17]([C:14]3[CH2:15][CH2:16][C:11]4[N:12]([C:8]([C:7]([F:6])([F:33])[F:34])=[N:9][N:10]=4)[N:13]=3)[CH2:18][CH2:19]2)=[CH:24][CH:25]=1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of methanesulfonyl chloride (0.158 mL, 2.04 mmol) in DCM (1 mL) was added dropwise to a stirred solution of 2-(4-{1-[3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenoxy)ethanol (695 mg, 1.70 mmol) and triethylamine (0.473 mL, 3.40 mmol) in DCM (7 mL) cooled to 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 15 minutes, then warmed to room temperature and stirred for a further 15 minutes. The reaction mixture was diluted with DCM (50 mL), and washed with water (50 mL) and saturated brine (25 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford 2-(4-{1-[3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenoxy)ethyl methanesulfonate (796 mg, 96%).

Workup

temperaturewarmed to room temperature
stirringstirred for a further 15 minutes
washwashed with water (50 mL) and saturated brine (25 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-2795360c609b4c38b4715ee1c204b5d3
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258140B2

Reaction notes

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