Sodium Bicarbonate → HCID 59331372, compound

HRID 1882095Notes

Reaction equation

HRID 1882095 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](=O)[CH2:8][CH2:9][C:10](=O)[CH:11]([C:19]2[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][N:20]=2)[CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:4][CH:3]=1.C([O-])(=O)C.[NH4+:33].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[S:6][C:5]([C:7]2[NH:33][C:10]([CH:11]([C:19]3[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][N:20]=3)[CH2:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:9][CH:8]=2)=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 593315881-(5-Chloro-2-thiazolyl)-5-[5-(methylthio)-2-pyridinyl]-6-(tetrahydro-2H-pyran-4-yl)-1,4-hexanedione

Product 1

HCID 59331372HCID 59331372, compoundYield 104.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 1-(5-chloro-1,3-thiazol-2-yl)-5-[5-(methylsulfanyl)pyridin-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (83.9 mg) in acetic acid (1.8 mL) was added ammonium acetate (278 mg), and the mixture was stirred at 110° C. for 1 hr. After cooling to room temperature, the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (83.9 mg, yield 89%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. dry with materialThe ethyl acetate layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ab3a26c180d34b18b07b66b92ac33e5c
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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