Ethyl Acetate → HCID 68525449, compound

HRID 884181Notes

Reaction equation

[CH2:1]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:36]=[CH:35][C:22]([O:23][C:24]3[N:29]=[CH:28][C:27](OS(C)(=O)=O)=[CH:26][CH:25]=3)=[CH:21][CH:20]=2)=[O:18])[CH2:13][CH2:12]1)[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.[F:37][C:38]([F:47])([F:46])[C:39]1[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=1.[C:48](=O)(O)[O-].[Na+].C(OCC)(=O)C>C1COCC1>[F:37][C:38]([F:46])([F:47])[C:39]1[CH:40]=[CH:41][C:42]([NH:45][CH2:48][C:27]2[CH:26]=[CH:25][C:24]([O:23][C:22]3[CH:35]=[CH:36][C:19]([C:17]([N:14]4[CH2:15][CH2:16][N:11]([CH2:1][C:2]5[CH:10]=[CH:9][C:8]6[O:7][CH2:6][O:5][C:4]=6[CH:3]=5)[CH2:12][CH2:13]4)=[O:18])=[CH:20][CH:21]=3)=[N:29][CH:28]=2)=[CH:43][CH:44]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Methanesulfonic acid 6-[4-(4-piperonylpiperazine-1-carbonyl)phenoxy]pyridin-3-yl ester (0.433 g, 0.824 mmol) and 4-trifluoromethyl phenylamine (0.310 mL, 2.47 mmol) were mixed together, and the resulting mixture was stirred for 2 hours at 100° C. The formed yellow mass was stirred together with a saturated sodium bicarbonate solution, ethyl acetate and THF (20 ml of each). The organic layer was collected, washed with brine, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=50:1), to thereby yield 0.236 g of the title compound.

Workup

customThe organic layer was collected
washwashed with brine
dry with materialdried over anhydrous magnesium sulfate
customevaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=50:1)

Sources & evidence

ORD record: ord-835b5ff1ed2e41eea0fdeaf274086fed
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236826B2

Reaction notes

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