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

HRID 33886

反応式

HRID 33886 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fd40ee35efc44dc184a867c4e954f280
出典データセット
uspto-grants-2008_09
特許番号
US07429665B2

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