Potassium Carbonate → HCID 178522807, compound

HRID 526569Notes

Reaction equation

HRID 526569 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([NH:17][NH:18][CH:19]=[C:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[C:21](OC)=[O:22])=N[CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31](=O)([O-])[O-].[K+].[K+]>C(O)C.C(OCC)(=O)C>[CH2:1]([NH:8][C:9](=[O:10])[C:11]1[CH:16]=[CH:31][C:14]([N:17]2[C:21]([OH:22])=[C:20]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH:19]=[N:18]2)=[CH:13][CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 131732884HCID 131732884, compound

Product 1

HCID 178522807HCID 178522807, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combined methyl 3-(2-(5-(benzylcarbamoyl)pyridin-2-yl)hydrazinyl)-2-(pyridin-2-yl)acrylate (110 mg, 0.273 mmol) and potassium carbonate (56.5 mg, 0.409 mmol) in ethanol (10 mL) and heated at 60° C. for 1 hour. The precipitate was filtered and washed with ethanol to give an off-white solid. This solid was then dissolved in ethyl acetate. The organic layer was washed with water, dried and concentrated to give the title compound as a yellow solid. (60 mg, 59%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.50 (d, J=6.06 Hz, 2H), 6.69 (ddd, J=7.07, 4.80, 1.26 Hz, 1H), 7.19-7.30 (m, 1H), 7.34 (d, J=4.55 Hz, 4H), 7.44 (ddd, J=8.21, 7.20, 2.02 Hz, 1H), 7.85 (s, 1H), 8.10-8.19 (m, 2H), 8.19-8.25 (m, 1H), 8.64 (dd, J=8.84, 0.76 Hz, 1H), 8.84 (dd, J=2.53, 0.76 Hz, 1H), 9.04 (t, J=5.81 Hz, 1H). MS m/z [M+H]+ 372.4

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with ethanol
  3. customto give an off-white solid
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7cd87f08d6434b689c313b4d8bd48e76
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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