Phenylacetylene → N-isopropyl-1-[3-(3-pyridinylethynyl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide

HRID 351733Notes

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]([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]([C:3]2[CH:4]=[CH:5][CH:6]=[C:1]([C:7]#[C:8][C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[CH:2]=2)[CH:23]=1)=[O:21])([CH3:17])[CH3:18]

Participants

Reactant 3

HCID 10821Phenylacetylene

HCID 122863-Bromopyridine

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

Product 1

HCID 10201499N-isopropyl-1-[3-(3-pyridinylethynyl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide

Procedure

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

Sources & evidence

ORD record: ord-50cc7f49d1da4a3aa35feee06c5387b8
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743802B2

Reaction notes

Loading…