Potassium Carbonate → HCID 71616414, compound

HRID 930841Notes

Reaction equation

HRID 930841 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH:11]=[CH:12][C:13]=2[O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]2[CH:26]=[CH:27][N:28](S(C3C=CC(C)=CC=3)(=O)=O)[C:4]=2[C:3]1=[O:39].[C:40](=O)([O-])[O-].[K+].[K+]>CO.O>[CH3:40][N:21]([C:10]1[CH:11]=[CH:12][C:13]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:8]([C:6]2[C:5]3[CH:26]=[CH:27][NH:28][C:4]=3[C:3](=[O:39])[N:2]([CH3:1])[CH:7]=2)[CH:9]=1)[S:22]([CH3:25])(=[O:23])=[O:24]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 89657305HCID 89657305, compound

Product 1

HCID 71616414HCID 71616414, compoundYield 14.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of Example 7d (0.113 g, 0.2 mmol) and potassium carbonate (0.111 g, 0.800 mmol) in methanol (0.9 mL) and water (0.1 mL) was heated at 100° C. for 1 hour. The reaction was partitioned between ethyl acetate and water adjusting the pH to 7. The organic layer was separated, dried (Na2SO4), filtered and concentrated. The residue was purified by reverse phase HPLC (C18, 10-100% CH3CN/water (0.1% TFA)) to afford the title compound (0.012 g, 14%). 1H NMR (300 MHz, DMSO-d6) δ 2.99 (s, 3H) 3.27 (s, 3H) 3.51 (s, 3H) 6.27-6.32 (m, 1H) 6.93 (d, J=7.80 Hz, 2H) 6.99 (d, J=8.82 Hz, 1H) 7.03-7.10 (m, 1H) 7.25-7.34 (m, 4H) 7.40 (dd, J=8.65, 2.88 Hz, 1H) 7.55 (d, J=2.71 Hz, 1H) 12.01 (s, 1H). MS (ESI+) m/z 424 [M+H]+.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water adjusting the pH to 7
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by reverse phase HPLC (C18, 10-100% CH3CN/water (0.1% TFA))

Sources & evidence

ORD record
ord-f2fa91e30ea64baca1a1e05086e6ce68
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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