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

HRID 2381135Notes

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)[CH:15]=[CH: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[CH:15]=[CH: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 (2.74 mL, 35.46 mmol) in DCM (40 mL) was added dropwise to a stirred solution of 2-(4-{1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenoxy)ethanol (12.04 g, 29.55 mmol) and triethylamine (8.24 mL, 59.11 mmol) in DCM (120 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 (100 mL), and washed with water (250 mL) and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to give 2-(4-{1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenoxy)ethyl methanesulfonate (14.32 g, 100%) as a solid.

Workup

temperaturethen warmed to room temperature
stirringstirred for a further 15 minutes
washwashed with water (250 mL) and saturated brine (100 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-a436a3896dbd48feb2be72585ddac74d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258140B2

Reaction notes

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