1,2-Dichloroethane → 6-((6,7-bis(methoxy)-4-quinolinyl)oxy)-N-(5-methyl-3-isoxazolyl)-1-naphthalenecarboxamide

HRID 1925320Notes

Reaction equation

HRID 1925320 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([C:26](Cl)=[O:27])=[CH:21][CH:20]=[CH:19]2.NC1[O:34][N:33]=[C:32](C)[CH:31]=1.C([N:38](CC)CC)C.Cl[CH2:44][CH2:45]Cl>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([C:26]([NH:38][C:32]1[CH:31]=[C:44]([CH3:45])[O:34][N:33]=1)=[O:27])=[CH:21][CH:20]=[CH:19]2

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 845905-Amino-3-methylisoxazoleHCID 248229436-(6,7-Dimethoxyquinolin-4-yloxy)-1-naphthoyl chloride

Product 1

HCID 248244466-((6,7-bis(methoxy)-4-quinolinyl)oxy)-N-(5-methyl-3-isoxazolyl)-1-naphthalenecarboxamide

Conditions

Temperature
80 °C

Procedure

A 16×100 mm resealable vial with stir-bar was charged with 1,2-dichloroethane (3.0 mL), 6-(6,7-dimethoxyquinolin-4-yloxy)-1-naphthoyl chloride (0.15 g, 0.38 mmol), and 5-amino-3-methylisoxazole (0.045 g, 0.46 mmol). To the suspension was added triethylamine (0.13 mL, 0.95 mmol) and N,N-dimethylaminopyridine (0.005 g, 0.04 mmol). The mixture stirred at 80° C. for 15 h and was then cooled to RT. The reaction mixture was concentrated and the residue was purified by column chromatography on silica gel (eluting with 2% methanol in dichloromethane) to afford 6-((6,7-bis(methoxy)-4-quinolinyl)oxy)-N-(5-methyl-3-isoxazolyl)-1-naphthalenecarboxamide as an off-white solid. MS (ESI, pos. ion) m/z: 456.1 (M+H). Mass Calc'd for C29H26FN3O5: 455.468

Workup

  1. temperaturewas then cooled to RT
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by column chromatography on silica gel (eluting with 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-6ca134bde70b49f1bbb8796c5e1e7621
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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