Potassium Carbonate → HCID 86625198, compound

HRID 419564Notes

Reaction equation

HRID 419564 reaction equation
C(O)(=O)C.[CH2:5]([O:7][C:8]1[CH:13]=[C:12]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:11]=[CH:10][C:9]=1[NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH3:6].[CH:27]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH2:28].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CO>[CH2:5]([O:7][C:8]1[CH:13]=[C:12]([CH:14]2[CH2:19][CH2:18][N:17]([CH2:28][CH2:27][S:29]([CH3:32])(=[O:31])=[O:30])[CH2:16][CH2:15]2)[CH:11]=[CH:10][C:9]=1[NH:20][C:21](=[O:26])[C:22]([F:23])([F:24])[F:25])[CH3:6]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 19354Methyl vinyl sulfoneHCID 86625197HCID 86625197, compound

Product 1

HCID 86625198HCID 86625198, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent

Procedure

To N-[2-(ethyloxy)-4-(4-piperidinyl)phenyl]-2,2,2-trifluoroacetamide acetate (2.2 g, 5.9 mmol) and methyl vinyl sulfone (0.74 g, 7.0 mmol) in DCM (50 mL) was added K2CO3 (1.2 g, 8.8 mmol). A few drops of MeOH were added to help solubilize the reagents. The reaction was stirred in a sealed tube three h. The reaction was filtered then purified by silica gel chromatography. The desired fractions were combined, and the solvent was removed under vacuum to provide the title compound of step F as a white solid (1.4 g, 3.3 mmol, 58%). 1H NMR (400 MHz, DMSO-d6) δ 8.52 (br s, 1H), 8.18 (d, J=8.2 Hz, 1H), 6.81 (dd, J=8.2, 1.6 Hz, 1H), 6.73 (d, J=1.6 Hz, 1H), 4.11 (q, J=7.0 Hz, 2H), 3.15 (t, J=6.6 Hz, 2H), 3.02 (s, 3H), 3.00 (d, J=11.7 Hz, 2H), 2.88 (t, J=6.6 Hz, 2H), 2.52-2.42 (m, 1H), 2.18-2.10 (m, 2H), 1.84 (d, J=12.8 Hz, 2H), 1.73-1.60 (m, 2H), 1.44 (t, J=7.0 Hz, 3H).

Workup

  1. filtrationThe reaction was filtered
  2. customthen purified by silica gel chromatography
  3. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-2e9b4ee6c98a48ecb87e613f423a8d17
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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