Diisopropylethylamine → 4-[4-[3-(Trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazin-1-yl]phenol

HRID 1675105Notes

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

Participants

Conditions

Temperature: 80 °C

Procedure

DIPEA (12.15 mL, 69.78 mmol) was added to 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (10.35 g, 46.52 mmol) and 1-(4-hydroxyphenyl)piperazine (CAS 56621-48-8, 9.12 g, 51.17 mmol) in DMF (80 mL). The resulting solution was stirred at 80° C. for 1 hour. The reaction mixture was cooled to room temperature, evaporated to dryness and the residue re-dissolved in DCM (250 mL). The solution was washed with water (200 mL), dried over MgSO4 and evaporated to afford crude product, which was triturated with diethyl ether. The resulting solid was collected by filtration and dried under vacuum to give 4-[4-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazin-1-yl]phenol (14.27 g, 84%) as a solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
customevaporated to dryness
dissolutionthe residue re-dissolved in DCM (250 mL)
washThe solution was washed with water (200 mL)
dry with materialdried over MgSO4
customevaporated
customto afford crude product, which
customwas triturated with diethyl ether
filtrationThe resulting solid was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-c93a8528151d4897b6645b5028db4036
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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