Potassium Carbonate → HCID 178509608, compound

HRID 526570Notes

Reaction equation

HRID 526570 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([NH:17][N:18]=[CH:19][CH:20]([C:26]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=2)[C:21](OCC)=[O:22])=[N:15][CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:1]([NH:8][C:9](=[O:10])[C:11]1[CH:12]=[CH:13][C:14]([N:17]2[C:21]([OH:22])=[C:20]([C:26]3[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=3)[CH:19]=[N:18]2)=[N:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 117601263HCID 117601263, compound

Product 1

HCID 178509608HCID 178509608, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combined ethyl 3-(2-(5-(benzylcarbamoyl)pyridin-2-yl)hydrazono)-2-(4-cyanophenyl)propanoate (90 mg, 0.204 mmol) and potassium carbonate (42.3 mg, 0.306 mmol) in ethanol (2 mL) and heated for 1 hour at 60° C. The reaction mixture was evaporated to give a residue which was purified by HPLC (ZQ9, Prep-TFA-50-55, Rt 4.54 min) to give the title compound (5 mg, 6%) as an off-white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 4.69 (d, J=5.56 Hz, 2H), 6.37 (br. s., 1H), 7.30-7.42 (m, 5H), 7.62-7.69 (m, 2H), 7.77-7.83 (m, 2H), 7.91 (s, 1H), 8.02 (d, J=8.08 Hz, 1H), 8.32 (dd, J=8.84, 2.27 Hz, 1H), 8.80 (d, J=1.77 Hz, 1H). MS m/z [M+H]+ 396.3.

Workup

  1. customThe reaction mixture was evaporated
  2. customto give a residue which
  3. customwas purified by HPLC (ZQ9, Prep-TFA-50-55, Rt 4.54 min)

Sources & evidence

ORD record
ord-8bad9983835a46009268b6f525c9d477
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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