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 phenylamide

HRID 1029186Notes

Reaction equation

HRID 1029186 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]=[CH:32][CH:31]=1)=[C:28]=[O:29]>>[C:30]1([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]=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 7672Phenyl isocyanateHCID 698108831-(3,4-Dihydro-2H-benzo[1,4]oxazin-7-yloxy)-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 698118837-(6-Oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-2,3-dihydro-benzo[1,4]oxazine-4-carboxylic acid phenylamideYield 7.7%

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 isocyanato benzene (26 mg, 0.22 mmol) to provide 223 (5 mg, 7% yield) as a tan solid. LC-MS (M+H=465, obsd.=465).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-677ac0db55e1431a9165c57b4369523c
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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