Ethyl Acetate → HCID 68525449, compound

HRID 1932537Notes

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-3fb2a97121b742549f3a6468a79b2374
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188277B2

Reaction notes

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