3-(Trifluoromethyl)phenyl isocyanate → 7-(6-Oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-2,3-dihydro-benzo[1,4]oxazine-4-carboxylic acid (3-trifluoromethyl-phenyl)-amide

HRID 1029187Notes

Reaction equation

HRID 1029187 reaction equation
[O:1]1[C:6]2[CH:7]=[C:8]([O:11][C:12]3[CH:21]=[CH:20][N:19]=[C:18]4[C:13]=3[C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16](=[O:22])[NH:17]4)[CH:9]=[CH:10][C:5]=2[NH:4][CH2:3][CH2:2]1.[N:27]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=1)=[C:28]=[O:29]>>[F:37][C:36]([F:38])([F:39])[C:32]1[CH:31]=[C:30]([NH:27][C:28]([N:4]2[C:5]3[CH:10]=[CH:9][C:8]([O:11][C:12]4[CH:21]=[CH:20][N:19]=[C:18]5[C:13]=4[C:14]4[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=4[C:16](=[O:22])[NH:17]5)=[CH:7][C:6]=3[O:1][CH2:2][CH2:3]2)=[O:29])[CH:35]=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 698108831-(3,4-Dihydro-2H-benzo[1,4]oxazin-7-yloxy)-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 684032177-(6-Oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-2,3-dihydro-benzo[1,4]oxazine-4-carboxylic acid (3-trifluoromethyl-phenyl)-amideYield 22.8%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 221 using 218 (50 mg, 0.14 mmol) and 1-isocyanato-3-trifluoromethyl-benzene (41 mg, 0.22 mmol) to provide 224 (17 mg, 22% yield) as a tan solid. LC-MS (M+H=533, obsd.=533).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-c3d8dc319c9b46b497b5380156b75053
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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