Diisopropylethylamine → HCID 67341147, compound

HRID 1675136Notes

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.[N:24]1([C:30]2[CH:40]=[CH:39][C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:32][CH:31]=2)[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>CN(C=O)C>[F:21][C:20]([F:23])([F:22])[C:17]1[N:15]2[N:16]=[C:11]([N:27]3[CH2:26][CH2:25][N:24]([C:30]4[CH:31]=[CH:32][C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:39][CH:40]=4)[CH2:29][CH2:28]3)[CH:12]=[CH:13][C:14]2=[N:19][N:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

DIPEA (2.348 mL, 13.48 mmol) was added to 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (2 g, 8.99 mmol) and ethyl 4-(piperazin-1-yl)benzoate (2.316 g, 9.89 mmol, CAS 80518-57-6) in DMF (20 mL). The resulting solution was stirred at 80° C. for 2 hours. The reaction mixture was cooled to room temperature, then evaporated to dryness and redissolved in DCM (150 mL) and washed with water (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product which was triturated with ether. The solid was collected by filtration and dried under vacuum to give ethyl 4-[4-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazin-1-yl]benzoate (3.40 g, 90%) as a solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
customevaporated to dryness
dissolutionredissolved in DCM (150 mL)
washwashed with water (100 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customevaporated
customto afford crude product which
customwas triturated with ether
filtrationThe solid was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-305b70286d234448a491433de4c8d34e
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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