Potassium Carbonate → HCID 24990479, compound

HRID 1878680Notes

Reaction equation

HRID 1878680 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=CC1.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 69268181HCID 69268181, 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-3c185b7c9825468888c9522bcda5ae30
Source dataset
uspto-grants-2012_11
Patent number
US08314119B2

Reaction notes

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