Potassium Carbonate → HCID 51347482, compound

HRID 1968703Notes

Reaction equation

HRID 1968703 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH:13]=[C:12]([C:14](OCC)=[O:15])[C:11](=S)[C:10]3[CH2:20][CH2:21][CH2:22][C:9]2=3)=[CH:3][CH:2]=1.Cl.[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH:37][NH2:38].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:1]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:2]=[CH:3][C:4]([CH2:7][N:8]2[CH:13]=[C:12]3[C:14](=[O:15])[N:37]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[F:30])[N:38]=[C:11]3[C:10]3[CH2:20][CH2:21][CH2:22][C:9]2=3)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)HCID 86667833HCID 86667833, compound

Product 1

HCID 51347482HCID 51347482, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-(biphenyl-4-ylmethyl)-4-thioxo-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carboxylate (0.30 g, 0.77 mmol) was suspended in ethanol (10 mL) and treated with 2-fluorophenylhydrazine hydrochloride (0.38 g, 2.3 mmol, 3 equiv) and potassium carbonate (0.64 g, 4.6 mmol, 6 equiv). The mixture was placed into a preheated oil bath at 80° C. for 24 hours, cooled to ambient temperature and concentrated in vacuo. The residue was treated with water (20 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (100:0 to 90:10; chloroform:methanol), providing the titled compound: 1H-NMR (400 MHz, CDCl3) δ 8.29 (1H, s), 7.61-7.56 (5H, m), 7.47-7.44 (2H, m), 7.40-7.30 (2H, m), 7.21-7.19 (2H, m), 5.20 (2H, s), 3.08 (2H, t, J=7.5 Hz), 2.94 (2H, t, J=7.5 Hz), 2.23 (2H, quin, J=7.5 Hz) ppm; low resolution mass spectrometry (ES+) m/z 436.1 [(M+H)+; calculated for C28H23FN3O: 436.2].

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with water (20 mL)
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialThe combined organic extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (100:0 to 90:10; chloroform:methanol)

Sources & evidence

ORD record
ord-83802a890d46462aaa6fad53becedf5e
Source dataset
uspto-grants-2013_04
Patent number
US08426438B2

Reaction notes

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