Sodium Bicarbonate → HCID 178456892, compound

HRID 1620512Notes

Reaction equation

HRID 1620512 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[CH2:13][CH:12]2[CH2:14][CH:8]([CH2:9][CH:10]([CH:15]=O)[CH2:11]2)[CH2:7]1.[CH2:27]([NH:30][C:31]1[CH2:35][S:34][C:33](=[O:36])[N:32]=1)[C:28]#[CH:29].C([O-])(=O)C.[NH2+]1CCCCC1.C(=O)([O-])O.[Na+]>CC(O)C>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[CH2:7][CH:8]2[CH2:14][CH:12]([CH2:11][CH:10](/[CH:15]=[C:35]3/[C:31]([NH:30][CH2:27][C:28]#[CH:29])=[N:32][C:33](=[O:36])[S:34]/3)[CH2:9]2)[CH2:13]1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 3014295Piperidinium acetateHCID 866787043-[2,4-Bis(trifluoromethyl)benzyl]-3-azabicyclo[3.3.1]nonane-7-carbaldehydeHCID 178456890HCID 178456890, compound

Product 1

HCID 178456892HCID 178456892, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-[2,4-bis(trifluoromethyl)benzyl]-3-azabicyclo[3.3.1]nonane-7-carbaldehyde (173.9 mg) and 4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one (141 mg) in 2-propanol (2.29 mL) was added piperidinium acetate (66.6 mg). The reaction mixture was stirred at 60° C. overnight, allowed to cool to room temperature, poured into saturated aqueous sodium hydrogen carbonate solution, 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 (NH, ethyl acetate/hexane) and recrystallized from ethyl acetate/hexane to give the title compound (36.4 mg).

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
  7. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-31d68afab5d34402b880e415b0d602da
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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