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

HRID 2113574Notes

Reaction equation

HRID 2113574 reaction equation
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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-34eb26f98844441dac8316eb07e6c267
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

Loading…