Ethanolamine → HCID 14502084, compound

HRID 1723090Notes

Reaction equation

[C:1]1([N:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]3O[CH2:18][CH2:19][C:9]=3[C:8]2=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OCCN.[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[C:1]1([N:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]3[N:32]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:18][CH2:19][C:9]=3[C:8]2=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 3

HCID 700Ethanolamine

HCID 7504Benzylamine

HCID 13934590HCID 13934590, compound

Product 1

HCID 14502084HCID 14502084, compound

Procedure

This procedure will also produce 1,2,3,5-tetrahydro-1-(n-butyl)-5-phenyl-4H-Pyrrolo[3,2-c][1,8]naphthyridin-4-one when 1-phenyl-3-(2-hydroxyethyl)-4-hydroxy-[1,8]naphthyridin-2-one is substituted for 3,5-dihydro-5-phenyl-furo[3,2-c][1,8]naphthyridin-4(2H)-one and n-butylamine is substituted for benzylamine. Furthermore, 1,2,3,5-tetrahydro-5-(3-chlorophenyl)-1-(2-hydroxyethyl)-2-methyl-4H-pyrrolo[3,2-c][1,8]naphthyridin-4-one may be produced by this procedure when 1-(3-chlorophenyl)-4-hydroxy-3-(2-hydroxypropyl)-[1,8]naphthyridin-2-one is substituted for 3,5-dihydro-5-phenyl-furo[3,2-c][1,8]naphthyridin-4(2H)-one and 2-hydroxyethylamine is substituted for benzylamine.

Sources & evidence

ORD record: ord-0a420056e2044560a41bdf310cee5f4b
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04859669

Reaction notes

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