3-Bromoquinoline → 1-[3-(1-Oxido-3-pyridinylethynyl)phenyl]-1,4-dihydro[1,8]naphthyridin4-one-3-carboxamide

HRID 351754Notes

Reaction equation

HRID 351754 reaction equation
C([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[CH:25])[CH:19]=2)[CH:8]=1)=[O:6])(C)C.Br[C:27]1[CH:28]=[N+:29]([O-:33])[CH:30]=[CH:31][CH:32]=1.BrC1C=NC2C(C=1)=CC=CC=2>>[O-:33][N+:29]1[CH:30]=[CH:31][CH:32]=[C:27]([C:25]#[C:24][C:20]2[CH:19]=[C:18]([N:9]3[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][N:11]=4)[C:16](=[O:17])[C:7]([C:5]([NH2:4])=[O:6])=[CH:8]3)[CH:23]=[CH:22][CH:21]=2)[CH:28]=1

Participants

4

Reactant 3

HCID 214133-BromoquinolineHCID 142763Pyridine, 3-bromo-, 1-oxideHCID 9880627n-Isopropyl-1-(3-ethynylphenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide

Product 1

HCID 102712331-[3-(1-Oxido-3-pyridinylethynyl)phenyl]-1,4-dihydro[1,8]naphthyridin4-one-3-carboxamide

Procedure

Following the procedure of example 19, but substituting the 1-(3-ethynylphenyl)-1,4-dihydro[1,8]naphthyridin4-one-3-carboxamide from Step 3 for N-Isopropyl-1-(3-ethynylphenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide and 3-bromopyridine N-oxide for 3-bromoquinoline, the 1-[3-(1-oxido-3-pyridinylethynyl)phenyl]-1,4-dihydro[1,8]naphthyridin4-one-3-carboxamide was obtained as a white solid.

Sources & evidence

ORD record
ord-9139c5fdfcae4e40b8253295c836134e
Source dataset
uspto-grants-2004_06
Patent number
US06743802B2

Reaction notes

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