Water → HCID 86678853, compound

HRID 1620693Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH2:4][N:3]2[C:7](=[O:10])[S:8][CH2:9][C:2]=12.[F:11][C:12]([F:33])([F:32])[C:13]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:14]=1[CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([CH:22]=O)[CH2:18][CH2:17]1.C([O-])(=O)C.[NH2+]1CCCCC1.O>CC(O)C>[F:33][C:12]([F:11])([F:32])[C:13]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:14]=1[CH2:15][N:16]1[CH2:21][CH2:20][CH:19](/[CH:22]=[C:9]2\[S:8][C:7](=[O:10])[N:3]3[CH2:4][CH:5]=[CH:6][N:1]=[C:2]\23)[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4,8-dihydro[1,3]thiazolo[3,4-a]pyrimidin-6-one (38 mg) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (125 mg) in 2-propanol (2 mL) was added piperidinium acetate (54 mg) at room temperature. The reaction mixture was stirred at 60° C. overnight. The reaction mixture was added to water at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (38 mg).

Workup

extractionthe mixture was extracted with ethyl acetate
customThe organic layer was separated
washwashed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-0752810e65944a1c949604d98e4ba57a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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