8-Hydroxy-1,6-naphthyridine-7-carbonitrile → HCID 178515408, compound

HRID 1158627Notes

Reaction equation

HRID 1158627 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[NH:8][C:9]([C:12]3[C:21]([OH:22])=[C:20]4[C:15]([CH:16]=[CH:17][CH:18]=[N:19]4)=[CH:14][N:13]=3)=[N:10][N:11]=2)=[CH:4][CH:3]=1.[OH:25]C1C(C#N)=NC=C2C=1N=CC=C2>>[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]([NH:11][NH2:10])=[O:25])=[CH:4][CH:3]=1.[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[NH:8][C:9]([C:12]3[C:21]([OH:22])=[C:20]4[C:15]([CH:16]=[CH:17][CH:18]=[N:19]4)=[CH:14][N:13]=3)=[N:10][N:11]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 595135008-Hydroxy-1,6-naphthyridine-7-carbonitrileHCID 178515408HCID 178515408, compound

Product 2

HCID 37716122-(4-Fluorophenyl)acetohydrazideHCID 178515408HCID 178515408, compoundYield 16%

Procedure

7-[5-(4-Fluorobenzyl)-4H-1,2,4-triazol-3-yl]-1,6-naphthyridin-8-ol. In a similar manner to that described in example 1 from of 8-hydroxy-1,6-naphthyridine-7-carbonitrile (30 mg, 0.18 mmol) and 2-(4-fluorophenyl)acetic hydrazide (147 mg, 0.90 mmol) was formed the title compound (9 mg, 16%) as a yellow solid. 1H NMR (CDCl3/CD3OD): δ 9.14 (m, 1 H), 8.80 (s, 1 H), 8.28 (m, 1 H), 7.61 (dd, J=8.4, 4.5 Hz, 1 H), 7.33 (dd, J=8.7, 5.7 Hz, 2 H), 6.99 (t, J=8.7 Hz, 2 H), 4.17 (s, 2 H); 9F NMR (CDCl3/CD3OD): δ −116.72; MS m/z 344 (M+Na).

Sources & evidence

ORD record
ord-5fa6cebcf4784617b050fc31df34d78a
Source dataset
uspto-grants-2010_10
Patent number
US07812016B2

Reaction notes

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