Dichloromethane → 7-(6,7-dimethoxyquinolin-4-yloxy)-N-(isoxazol-3-yl)-2,3-dihydrobenzo[b][1,4]oxazine-4-carboxamide

HRID 1925357Notes

Reaction equation

HRID 1925357 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]=[CH:18][C:19]2[NH:24][CH2:23][CH2:22][O:21][C:20]=2[CH:25]=1.[O:26]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=O)[O:33]C2C=CC([N+]([O-])=O)=CC=2)=[N:27]1.C(Cl)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]=[CH:18][C:19]2[N:24]([C:32]([NH:31][C:28]3[CH:29]=[CH:30][O:26][N:27]=3)=[O:33])[CH2:23][CH2:22][O:21][C:20]=2[CH:25]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 248240487-(6,7-dimethoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazineHCID 675199914-Nitrophenyl isoxazol-3-ylcarbamate

Product 1

HCID 117512397-(6,7-dimethoxyquinolin-4-yloxy)-N-(isoxazol-3-yl)-2,3-dihydrobenzo[b][1,4]oxazine-4-carboxamide

Conditions

Temperature
35 °C

Procedure

To a solution of 7-(6,7-dimethoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine (100 mg, 0.2955 mmol) and 4-nitrophenyl isoxazol-3-ylcarbamate (294 mg, 1.182 mmol) in CH2Cl2 (3 mL) DIPEA (269 μL, 2.069 mmol) was added at RT. The reaction mixture was stirred at 35° C. for 15 h before the solution was concentrated in vacuo and purified with column chromatography using 100% EtOAc→10%→30%→50% 19:1 EtOAc:MeOH to yield the title compound. MS (ESI, pos. ion) m/z: 449 (M+1). Mass calc'd for C23H20N4O6: 448.44.

Workup

  1. concentrationwas concentrated in vacuo
  2. custompurified with column chromatography

Sources & evidence

ORD record
ord-0e5c9277521846c3b9c869d1498e3549
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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