1,2,3,5-tetrahydro-5-(3-chlorophenyl)-2-methyl-1-(phenylmethyl)-4H-pyrrolo[3,2-c][1,8]naphthyridin-4-one → 1,2,3,5-tetrahydro-5-(3-methoxyphenyl)-1-hydroxy-2-methyl-4H-pyrrolo[3,2-c][1,8]naphthyridin-4-one

HRID 982418Notes

Reaction equation

HRID 982418 reaction equation
Cl[C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11]3[N:18](CC4C=CC=CC=4)[CH:19]([CH3:21])[CH2:20][C:10]=3[C:9]2=[O:29])[CH:5]=[CH:6][CH:7]=1.Cl[C:31]1[CH:32]=[C:33]([N:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][N:45]=3)[C:40]([OH:47])=[C:39]([CH2:48][CH:49]([OH:51])[CH3:50])[C:38]2=[O:52])[CH:34]=[CH:35][CH:36]=1.[OH:53][C:54]1C2C(=NC=CC=2)NC(=O)C=1>>[CH3:40][O:47][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11]3[N:18]([OH:53])[CH:19]([CH3:21])[CH2:20][C:10]=3[C:9]2=[O:29])[CH:5]=[CH:6][CH:7]=1.[OH:47][C:40]1[C:41]2[C:46](=[N:45][CH:44]=[CH:43][CH:42]=2)[N:37]([C:33]2[CH:34]=[CH:35][CH:36]=[C:31]([O:53][CH3:54])[CH:32]=2)[C:38](=[O:52])[C:39]=1[CH2:48][CH:49]([OH:51])[CH3:50]

Participants

5

Reactant 3

HCID 200675971,2,3,5-tetrahydro-5-(3-chlorophenyl)-2-methyl-1-(phenylmethyl)-4H-pyrrolo[3,2-c][1,8]naphthyridin-4-oneHCID 547142824-Hydroxy-1,2-dihydro-1,8-naphthyridin-2-oneHCID 547362861-(3-Chlorophenyl)-3-(2-hydroxypropyl)-4-hydroxy-[1,8]naphthyridin-2-one

Product 2

HCID 200675981,2,3,5-tetrahydro-5-(3-methoxyphenyl)-1-hydroxy-2-methyl-4H-pyrrolo[3,2-c][1,8]naphthyridin-4-oneHCID 547294864-Hydroxy-1-(3-methoxyphenyl)-3-(2-hydroxypropyl)-[1,8]naphthyridin-2-one

Procedure

This procedure will also produce 1,2,3,5-tetrahydro-5-(3-chlorophenyl)-2-methyl-I-(phenylmethyl)-4H-pyrrolo[3,2-c][1,8]naphthyridin-4-one when 1-(3-chlorophenyl)-3-(2-hydroxypropyl)-4-hydroxy-[1,8]naphthyridin-2-one is substituted for 1-phenyl-3-(2-hydroxyethyl)-hydroxyethyl)-4-hydroxy-[1, 8]naphthyridin-2-one. Furthermore, 1,2,3,5-tetrahydro-5-(3-methoxyphenyl)-1-hydroxy-2-methyl-4H-pyrrolo[3,2-c][1,8]naphthyridin-4-one is produced by this procedure when 4-hydroxy-1-(3-methoxyphenyl)-3-(2-hydroxypropyl)-[1,8]naphthyridin-2-one is substituted for 1-phenyl-3-(2-hydroxyethyl)-4-hydroxy-[1,8]naphthyridin-2-one and hydroxylamine hydrochloride is substituted for benzylamine hydrochloride.

Sources & evidence

ORD record
ord-c66cfc1badb147ab853fe94ceabb3e30
Source dataset
uspto-grants-1991_02
Patent number
US04996212

Reaction notes

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