Water → Methyl 4-[1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]benzoate

HRID 1675095Notes

Reaction equation

CCN(C(C)C)C(C)C.Cl[C:11]1[CH:12]=[CH:13][C:14]2[N:15]([C:17]([C:20]([F:23])([F:22])[F:21])=[N:18][N:19]=2)[N:16]=1.[NH:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=2)[CH2:26][CH2:25]1.O>CC(N(C)C)=O>[F:21][C:20]([F:23])([F:22])[C:17]1[N:15]2[N:16]=[C:11]([N:24]3[CH2:29][CH2:28][CH:27]([C:30]4[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)[CH:12]=[CH:13][C:14]2=[N:19][N:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

DIPEA (88 mL, 505.27 mmol) was added to 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (45.0 g, 202.11 mmol) and methyl 4-(piperidin-4-yl)benzoate (48.75 g, 222.32 mmol) in DMA (250 mL). The resulting suspension was stirred at 100° C. for 1 hour then cooled to room temperature. The reaction mixture was added dropwise to water (1500 mL) with stirring. Stirring was continued for 10 minutes then the precipitate was collected by filtration, washed with water (300 mL) and ether (250 mL×2) and dried to afford methyl 4-[1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]benzoate (76 g, 93%) as a solid.

Workup

temperaturethen cooled to room temperature
stirringwith stirring
stirringStirring
waitwas continued for 10 minutes
filtrationthe precipitate was collected by filtration
washwashed with water (300 mL) and ether (250 mL×2)
customdried

Sources & evidence

ORD record: ord-6df5dab3fbf8442aa29f8380fd36bdd4
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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