Potassium Carbonate → HCID 86660000, compound

HRID 242015Notes

Reaction equation

HRID 242015 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]3[CH:20]=[N:21][C:22]([CH3:25])=[CH:23][CH:24]=3)=[N:17][CH:18]=1)[N:9]=[C:8]([C:26](OCC)=[O:27])[C:7]2=S.[NH:32]([CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]1[OH:40])[NH2:33].C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.C(OCC)(=O)C>[Cl:1][C:2]1[C:11]2[N:10]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([C:19]4[CH:20]=[N:21][C:22]([CH3:25])=[CH:23][CH:24]=4)=[N:17][CH:18]=3)[N:9]=[C:8]3[C:26](=[O:27])[N:32]([C@@H:34]4[CH2:39][CH2:38][CH2:37][CH2:36][C@H:35]4[OH:40])[N:33]=[C:7]3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 13403697HCID 13403697, compoundHCID 86660001HCID 86660001, compound

Product 1

HCID 86660000HCID 86660000, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 8-chloro-1-[(6′-methyl-2,3′-bipyridin-5-yl)methyl]-4-thioxo-1,4-dihydrocinnoline-3-carboxylate (26 mg, 0.0058 mmol), (±)-2-hydrazinylcyclohexanol (19 mg, 0.14 mmol, 2.5 equiv) and potassium carbonate (24 mg, 0.17 mmol, 3 equiv) were combined in dimethoxyethane (1 mL) and placed into an oil bath preheated to 90° C. for 90 minutes. The mixture was cooled to ambient temperature, diluted with ethyl acetate and washed once with water and brine. The organic layer was dried sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 90:10; chloroform:methanol), providing the titled compound as a deep red solid: 1H-NMR (400 MHz, CDCl3) δ 9.02 (1H, br s), 8.56 (1H, s), 8.21 (1H, d, J=9.1 Hz), 8.16 (1H, d, J=10.9 Hz), 7.65 (2H, d, J=7.5 Hz), 7.56 (1H, d, J=9.2 Hz), 7.43 (2H, t, J=7.5 Hz), 7.27-7.21 (1H, m), 6.33 (2H, s), 4.34-4.25 (1H, m), 4.11-4.02 (1H, m), 2.6 (3H, s), 2.26-2.17 (1H, m), 2.07-2.00 (1H, m), 1.92-1.79 (2H, m), 1.68-1.56 (2H, m), 1.52-1.39 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 501.1812 [(M+H)+; calculated for C27H25ClN6O2: 501.1800].

Workup

  1. customplaced into an oil bath
  2. washwashed once with water and brine
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel gradient chromatography (100:0 to 90:10; chloroform:methanol)

Sources & evidence

ORD record
ord-e052c49111f94d0da844bf097d743907
Source dataset
uspto-grants-2014_02
Patent number
US08653079B2

Reaction notes

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