3,4-dihydro-2H-benzo[b][1,4]oxazin-7-ol → 1-(3,4-Dihydro-2H-benzo[1,4]oxazin-7-yloxy)-5H-benzo[c][1,8]naphthyridin-6-one

HRID 1029181Notes

Reaction equation

HRID 1029181 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[O:17]1[C:22]2[CH:23]=[C:24]([OH:27])[CH:25]=[CH:26][C:21]=2[NH:20][CH2:19][CH2:18]1>>[O:17]1[C:22]2[CH:23]=[C:24]([O:27][C:2]3[CH:11]=[CH:10][N:9]=[C:8]4[C:3]=3[C:4]3[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=3[C:6](=[O:12])[NH:7]4)[CH:25]=[CH:26][C:21]=2[NH:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 193865643,4-dihydro-2H-benzo[b][1,4]oxazin-7-olHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 698108831-(3,4-Dihydro-2H-benzo[1,4]oxazin-7-yloxy)-5H-benzo[c][1,8]naphthyridin-6-oneYield 74%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 182 using Compound 83 (250 mg, 1.08 mmol) and 3,4-dihydro-2H-benzo[1,4]oxazin-7-ol (328 mg, 2.17 mmol) to provide 218 (276 mg, 74% yield) as a tan solid. LC-MS (M+H=346, obsd.=346).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-0eaf0ac0f91646d68415d01ed20b488b
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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