Phenylacetylene → N-cyclopropyl-4-oxo-1-(3-(2-(pyridin-3-yl)ethynyl)phenyl)-1,4-dihydro-1,8-naphthyridine-3-carboxamide

HRID 351734Notes

Reaction equation

HRID 351734 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.[CH:16]([NH:19][C:20]([C:22]1[C:31](=[O:32])[C:30]2[C:25](=[N:26][CH:27]=[CH:28][CH:29]=2)[N:24](C2C=CC=C(Br)C=2)[CH:23]=1)=[O:21])([CH3:18])[CH3:17]>>[CH:16]1([NH:19][C:20]([C:22]2[C:31](=[O:32])[C:30]3[C:25](=[N:26][CH:27]=[CH:28][CH:29]=3)[N:24]([C:3]3[CH:4]=[CH:5][CH:6]=[C:1]([C:7]#[C:8][C:10]4[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=4)[CH:2]=3)[CH:23]=2)=[O:21])[CH2:17][CH2:18]1

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 122863-BromopyridineHCID 129913181-(3-bromophenyl)-N-isopropyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Product 1

HCID 10136016N-cyclopropyl-4-oxo-1-(3-(2-(pyridin-3-yl)ethynyl)phenyl)-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Procedure

Following the procedure of Step 5 of EXAMPLE 1, but substituting N-cyclopropyl-1-(3-ethynylphenyl)- 1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide from EXAMPLE 6 for phenylacetylene and 3-bromopyridine for N-isopropyl-1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin4-one-3-carboxamide, the title compound was obtained as a solid.

Sources & evidence

ORD record
ord-4f7cb8f95107489ca81bbf7c0314197a
Source dataset
uspto-grants-2004_06
Patent number
US06743802B2

Reaction notes

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