Phenylhydrazine → HCID 52914156, compound

HRID 341033Notes

Reaction equation

HRID 341033 reaction equation
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=S)[C:10]([C:19]([O:21]CC)=O)=[CH:9]2)=[CH:3][CH:2]=1.[C:30]1([NH:36][NH2:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C>C(O)C>[C:1]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:2]=[CH:3][C:4]([CH2:7][N:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11]3=[N:37][N:36]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:19](=[O:21])[C:10]3=[CH:9]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 90495Di-tert-butyl dicarbonateHCID 86668673HCID 86668673, compound

Product 1

HCID 52914156HCID 52914156, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-(biphenyl-4-ylmethyl)-4-thioxo-1,4-dihydroquinoline-3-carboxylate [(Example 8, Step 2), 72 mg, 0.18 mmol] and phenylhydrazine (0.19 g, 1.8 mmol, 10 equiv) were combined in absolute ethanol (5 mL) and placed into a preheated oil bath at 75° C. for 18 hours. The mixture was cooled to ambient temperature and concentrated in vacuo. The residue was dissolved in dichloromethane (10 mL) and treated with di-tert-butyldicarbonate (0.30 g, 1.4 mmol, 7.8 equiv). After stirring for 5 hours at ambient temperature, the mixture was concentrated in vacuo and the residue was purified by silica gel gradient chromatography (100:0 to 95:5; dichloromethane:methanol), providing the titled compound: 1H-NMR (500 MHz, d6-DMSO) δ 9.17 (1H, s), 8.31 (1H, dd, J=7.8, 1.4 Hz), 8.22 (2H, d, J=7.6 Hz), 7.81 (1H, d, J=8.8 Hz), 7.67-7.62 (5H, m), 7.57 (1H, t, J=7.8 Hz), 7.48-7.40 (6H, m), 7.35 (1H, t, J=7.4 Hz), 7.20 (1H, t, J=7.4 Hz), 5.80 (2H, s) ppm; high resolution mass spectrometry (ES+) m/z 428.1757 [(M+H)+; calculated for C29H22N3O: 428.1758].

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (10 mL)
  3. concentrationthe mixture was concentrated in vacuo
  4. customthe residue was purified by silica gel gradient chromatography (100:0 to 95:5; dichloromethane:methanol)

Sources & evidence

ORD record
ord-44956d1d792d457abba5189cb0967c62
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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