Piperidinium acetate → HCID 178456894, compound

HRID 1620636Notes

Reaction equation

[F:1][C:2]([F:25])([F:24])[C:3]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[C:12](=[O:13])[CH2:11][CH2:10][CH:9]([CH:14]=O)[CH2:8][CH2:7]1.[CH2:26]([NH:29][C:30]1[CH2:34][S:33][C:32](=[O:35])[N:31]=1)[C:27]#[CH:28].C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:24][C:2]([F:25])([F:1])[C:3]1[CH:19]=[C:18]([C:20]([F:23])([F:21])[F:22])[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[CH2:7][CH2:8][CH:9](/[CH:14]=[C:34]2/[C:30]([NH:29][CH2:26][C:27]#[CH:28])=[N:31][C:32](=[O:35])[S:33]/2)[CH2:10][CH2:11][C:12]1=[O:13]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]-7-oxoazepane-4-carbaldehyde (1.00 g) and 4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one (0.63 g) in 2-propanol (10 mL) was added piperidinium acetate (0.40 g). The reaction mixture was stirred at 80° C. for 2 hr and concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.48 g).

Workup

concentrationconcentrated
additionWater was added to the residue
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-410c56fd6be14151b571ba61869b5d67
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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