Water → 6-[4-[4-[2-(1H-pyrazol-1-yl)ethoxy]phenyl]piperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine

HRID 1675150Notes

Reaction equation

[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.Br[CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:25]=[CH:26][C:27]4[N:28]([C:30]([C:33]([F:36])([F:35])[F:34])=[N:31][N:32]=4)[N:29]=3)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1.O>CN(C=O)C>[N:3]1([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:19][CH2:20][N:21]([C:24]4[CH:25]=[CH:26][C:27]5[N:28]([C:30]([C:33]([F:36])([F:34])[F:35])=[N:31][N:32]=5)[N:29]=4)[CH2:22][CH2:23]3)=[CH:14][CH:13]=2)[CH:7]=[CH:6][CH:5]=[N:4]1

Participants

Conditions

Temperature: 20 °C

Procedure

Sodium hydride (60% dispersion in oil, 16.97 mg, 0.42 mmol) was added to 1H-pyrazole (28.9 mg, 0.42 mmol) in DMF (2 mL) at 20° C. under nitrogen. The resulting suspension was stirred at 20° C. for 20 minutes. 6-[4-[4-(2-Bromoethoxy)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (100 mg, 0.21 mmol) was added and the reaction stirred at 20° C. for 1 hour. Water (25 mL) was then added and the resulting precipitate filtered off, washed with ether and dried overnight under vacuum at 50° C. to give 6-[4-[4-[2-(1H-pyrazol-1-yl)ethoxy]phenyl]piperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (66.0 mg, 68%) as a pale yellow solid.

Workup

stirringthe reaction stirred at 20° C. for 1 hour
filtrationthe resulting precipitate filtered off
washwashed with ether
customdried overnight under vacuum at 50° C.

Sources & evidence

ORD record: ord-663f91a8951b4eb3bc14e6959afc9392
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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