Diisopropylethylamine → 4-(4-Hydroxyphenyl)-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol

HRID 1675164

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

Participants

Conditions

Temperature: 80 °C

Procedure

DIPEA (1.174 mL, 6.74 mmol) was added to 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (1 g, 4.49 mmol) and 4-(4-hydroxyphenyl)piperidin-4-ol (0.955 g, 4.94 mmol) in DMF (10 mL). The resulting solution was stirred at 80° C. for 1 hour. The reaction mixture was cooled to room temperature then evaporated to dryness. The residues were triturated with water and the resulting solid collected by filtration, washed with further water followed by ether, then dried under vacuum to afford 4-(4-hydroxyphenyl)-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol (1.680 g, 99%) as a solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
customthen evaporated to dryness
customThe residues were triturated with water
filtrationthe resulting solid collected by filtration
washwashed with further water
customdried under vacuum

Sources & evidence

ORD record: ord-0783dca6274643fb9353a91a520e9117
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Linked notes

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