Potassium Carbonate → HCID 24990479, compound

HRID 878453Notes

Reaction equation

HRID 878453 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]3[N:24]=[CH:23][C:22]([NH:25][C@@H:26]4[CH:33]5[CH2:34][N:29]6[CH2:30][CH:31]([CH2:35][CH:27]4[CH2:28]6)[CH2:32]5)=[CH:21][CH:20]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]2[N:24]=[CH:23][C:22]([NH:25][C@@H:26]3[CH:33]4[CH2:34][N:29]5[CH2:30][CH:31]([CH2:35][CH:27]3[CH2:28]5)[CH2:32]4)=[CH:21][CH:20]=2)=[CH:11]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68821600HCID 68821600, compound

Product 1

HCID 24990479HCID 24990479, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the product of Example 162A (50 mg, 0.103 mmol) and potassium carbonate (34 mg, 0.25 mmol) in methanol (3 mL) was heated to reflux for 90 minutes. After cooling, the solvent was removed, the residue was dissolved in water, and the mixture was extracted with ethyl acetate (3×). The combined extracts were washed with brine, dried (Na2SO4), filtered and concentrated to afford the free base of the title compound: 1H NMR (300 MHz, methanol-D4) δ ppm 1.68 (s, 1H), 1.86 (d, J=14.9 Hz, 2H), 1.96 (s, 2H), 2.29 (d, J=12.2 Hz, 2H), 3.09-3.29 (m, 8H), 3.81 (s, 1H), 7.01-7.24 (m, 3H), 7.40 (d, J=7.1 Hz, 1H), 7.50-7.61 (m, 2H), 7.98 (d, J=7.5 Hz, 1H), 8.07 (d, J=2.4 Hz, 1H). MS (DCI/NH3) m/z=345 (M+H)+.

Workup

  1. temperatureto reflux for 90 minutes
  2. temperatureAfter cooling
  3. customthe solvent was removed
  4. dissolutionthe residue was dissolved in water
  5. extractionthe mixture was extracted with ethyl acetate (3×)
  6. washThe combined extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-044cc557021b49dc835078a615e26cff
Source dataset
uspto-grants-2015_03
Patent number
US08987453B2

Reaction notes

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