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 1723089Notes

Reaction equation

HRID 1723089 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.C1(N2C3C(=CC=CN=3)[C:62]([OH:69])=C(CCO)C2=O)C=CC=CC=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:69])[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:69][CH3:62])[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 547236674-hydroxy-3-(2-hydroxyethyl)-1-phenyl-1,8-naphthyridin-2(1H)-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-1-(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)-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-942ea5b0cb244ca7a1bda04cc80f2b71
Source dataset
uspto-grants-1989_08
Patent number
US04859669

Reaction notes

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