Piperidinium acetate → HCID 178463973, compound

HRID 1620575Notes

Reaction equation

[CH2:1]([N:3]([CH2:15][CH3:16])[CH2:4]/[CH:5]=[CH:6]\[CH2:7][NH:8][C:9]1[CH2:13][S:12][C:11](=[O:14])[N:10]=1)[CH3:2].[F:17][C:18]([F:39])([F:38])[C:19]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:20]=1[CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([CH:28]=O)[CH2:24][CH2:23]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:39][C:18]([F:17])([F:38])[C:19]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:20]=1[CH2:21][N:22]1[CH2:27][CH2:26][CH:25](/[CH:28]=[C:13]2/[C:9]([NH:8][CH2:7]/[CH:6]=[CH:5]\[CH2:4][N:3]([CH2:1][CH3:2])[CH2:15][CH3:16])=[N:10][C:11](=[O:14])[S:12]/2)[CH2:24][CH2:23]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-{[(2Z)-4-(diethylamino)but-2-en-1-yl]amino}-1,3-thiazol-2(5H)-one (440 mg) in 2-propanol (5 mL) were added 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (617 mg) and piperidinium acetate (264 mg) at room temperature, and the reaction mixture was stirred at 60° C. for 4 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (164 mg).

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record: ord-fb7e24c4780d4c5fa210351de0db0100
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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