Tetrahydrofuran → 4-[(3-Isopropylphenyl)amino]-6-(2-morpholin-4-ylethoxy)-1,7-naphthyridine-3-carbonitrile

HRID 2113574ノート

反応式

HRID 2113574 の反応式
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:23])[CH3:22])[CH:16]=1.[OH:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C1COCC1>>[CH:21]([C:17]1[CH:16]=[C:15]([NH:14][C:5]2[C:4]3[C:9](=[CH:10][N:11]=[C:2]([O:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]#[N:13])[CH:20]=[CH:19][CH:18]=1)([CH3:23])[CH3:22]

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 611632-MorpholinoethanolHCID 691808106-Fluoro-4-[(3-isopropylphenyl)amino]-1,7-naphthyridine-3-carbonitrile

生成物 1

HCID 691856064-[(3-Isopropylphenyl)amino]-6-(2-morpholin-4-ylethoxy)-1,7-naphthyridine-3-carbonitrile収率 66%

実験手順

To 6-fluoro-4-[(3-isopropylphenyl)amino]-1,7-naphthyridine-3-carbonitrile (0.050 g, 0.16 mmol) was added a 1 M solution of freshly prepared alkoxide of N-(2-hydroxyethyl)morpholine in THF (1.88 mL, 1.88 mmol). The reaction was heated to reflux for 2 hours. The solvent was evaporated and water was added. Diethyl ehter and methylene chloride was added and crystals formed. The product was collected by filtration to give a yellow solid (0.044 g, 66%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.2 (d, J=6.8 Hz, 6 H) 2.5 (m, 2 H) 2.7 (t, J=5.8 Hz, 2 H) 2.9 (m, 1 H) 3.3 (m, 2 H) 3.6 (m, 4 H) 4.5 (t, J=5.8 Hz, 2 H) 7.1 (m, 3 H) 7.3 (t, J=8.7 Hz, 1 H) 7.8 (s, 1 H) 8.4 (s, 1 H) 9.0 (s, 1 H) 9.9 (s, 1 H).

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent was evaporated
  4. additionwater was added
  5. additionDiethyl ehter and methylene chloride was added
  6. customcrystals formed
  7. filtrationThe product was collected by filtration

出典と根拠

ORDレコード
ord-34eb26f98844441dac8316eb07e6c267
出典データセット
uspto-grants-2008_10
特許番号
US07432279B2

反応ノート

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