2,5-Dichloro-nicotinoyl chloride → 2,5-Dichloro-N-[3-fluoro-4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-nicotinamide

HRID 1029147Notes

Reaction equation

HRID 1029147 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:16]=[CH:15][N:14]=[C:13]3[C:8]=2[C:9]2[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=2[C:11](=[O:17])[NH:12]3)=[C:4]([F:24])[CH:3]=1.[Cl:25][C:26]1[N:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:27]=1[C:28](Cl)=[O:29]>>[Cl:25][C:26]1[N:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:27]=1[C:28]([NH:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:16]=[CH:15][N:14]=[C:13]3[C:8]=2[C:9]2[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=2[C:11](=[O:17])[NH:12]3)=[C:4]([F:24])[CH:3]=1)=[O:29]

Participants

3

Reactant 2

HCID 27999962,5-Dichloro-nicotinoyl chlorideHCID 581683451-(4-Amino-2-fluoro-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 581679832,5-Dichloro-N-[3-fluoro-4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-nicotinamideYield 45%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 180 using Compound 182 (50 mg, 0.16 mmol) and 2,5-dichloro-nicotinoyl chloride (36 mg, 0.17 mmol) to provide 183 (35 mg, 45% yield) as a dark solid. LC-MS (M+H=496, obsd.=496).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-a2713a867d404be3af43d0f30477a00b
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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