Dimethylformamide → HCID 68154167, compound

HRID 341100

Reaction equation

HRID 341100 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N+:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](Cl)=[C:11]([C:20]([O:22]CC)=O)[CH:10]=2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[NH:39][NH2:40].CN(C)C=O>O.COCCOC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]3=[N:40][N:39]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[CH3:32])[C:20](=[O:22])[C:11]3=[CH:10]2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 68153930HCID 68153930, compound

Product 1

HCID 68154167HCID 68154167, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

1-[(5-Bromopyridin-2-yl)methyl]-4-chloro-3-(ethoxycarbonyl)quinolinium salt (1.55 g, 3.51 mmol), potassium carbonate (2.63 g, 19.1 mmol, 5.4 equiv), and (2-methylphenyl)hydrazine hydrochloride (1.33 g, 8.38 mmol, 2.4 equiv) were combined in a mixture (1:1) of N,N-dimethylformamide:1,2-dimethoxyethane (25 mL) and placed into an oil bath preheated at 80° C. for 3 hours. The mixture was cooled to ambient temperature, poured into water (100 mL) and extracted with dichloromethane (2×100 mL). The combined organic extracts were dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 90:10; dichloromethane:methanol), providing the titled compound as a yellow solid: 1H-NMR (400 MHz, CD3OD) δ 8.97 (1H, s), 8.59 (1H, s), 8.33 (1H, d, J=7.8 Hz), 8.02-8.00 (1H, m), 7.78 (1H, d, J=9.0 Hz), 7.66-7.56 (2H, m), 7.48-7.37 (5H, m), 5.85 (2H, s), 2.28 (3H, s), ppm; low resolution mass spectrometry (ES+) m/z 446.8 [(M+H)+; calculated for C23H17BrN4O: 446.3].

Workup

  1. extractionextracted with dichloromethane (2×100 mL)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel gradient chromatography (100:0 to 90:10; dichloromethane:methanol)

Sources & evidence

ORD record
ord-873757eabe91491aab7c8f0885940f3c
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Linked notes

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