N-Dimethylaminomethylene-isonicotinamide → 2-[4-(5-Pyridin-4-yl-[1,2,4]triazol-1-yl)-phenoxymethyl]-quinoline

HRID 33886

Reaction equation

HRID 33886 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1.CN([CH:24]=[N:25][C:26](=O)[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)C>CO.C(O)(=O)C>[N:30]1[CH:31]=[CH:32][C:27]([C:26]2[N:19]([C:16]3[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:1]=4)=[CH:18][CH:17]=3)[N:20]=[CH:24][N:25]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 12569643N-Dimethylaminomethylene-isonicotinamideHCID 152250684-(Quinolin-2-ylmethoxy)phenylhydrazine

Product 1

HCID 116608802-[4-(5-Pyridin-4-yl-[1,2,4]triazol-1-yl)-phenoxymethyl]-quinolineYield 21.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Isonicatinamide (4.15 g) was heated in 35 ml of N,N-Dimethylformamide diethyl acetal at reflux for 3 h. The reaction mixture was cooled to ambient temperature and concentrated to give 5.02 g of N-Dimethylaminomethylene-isonicotinamide. To a solution of [4-(Quinolin-2-ylmethoxy)-phenyl]-hydrazine (3.16 g) in methanol (30 mL) and acetic acid (2.5 mL) was added N-Dimethylaminomethylene-isonicotinamide (1.10 g) and the reaction mixture heated at reflux for 72 h. The reaction mixture was concentrated onto silica gel and purified by flash chromatography to provided the title compound (514 mg). 1H NMR (400 MHz, CDCl3) δ 8.60 (d, J=5.8 Hz, 2 H), 8.22 (d, J=8.7 Hz, 1 H), 8.10 (s, 1H), 8.07 (d, J=8.7 Hz, 1H), 7.85 (d, J=7.1 Hz, 1H), 7.76 (m, 1 H), 7.66 (d, J=8.3 Hz, 1 H), 7.56 (m, 1 H), 7.56 (m, 1H), 7.38 (d, J=6.2 Hz, 2 H), 7.26 (d, J=8.7Hz, 2H), 7.11 (d, J=9.1 Hz, 2H), 5.42 (s, 2H); MS: (M+H m/z=380.3).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 72 h
  3. concentrationThe reaction mixture was concentrated onto silica gel
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-fd40ee35efc44dc184a867c4e954f280
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Linked notes

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