2-(4-Fluorophenyl)acetohydrazide → 5-(1,1-dioxothiazinan-2-yl)-7-[5-[(4-fluorophenyl)methyl]-4H-1,2,4-triazol-3-yl]-1,6-naphthyridin-8-ol

HRID 1158631Notes

Reaction equation

HRID 1158631 reaction equation
[O:1]=[S:2]1(=[O:21])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[N:17]=[C:16]([C:18]#[N:19])[C:15]([OH:20])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([NH:32][NH2:33])=O)=[CH:25][CH:24]=1>>[O:21]=[S:2]1(=[O:1])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[N:17]=[C:16]([C:18]2[NH:19][C:30]([CH2:29][C:26]3[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=3)=[N:32][N:33]=2)[C:15]([OH:20])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2

Participants

3

Reactant 2

HCID 37716122-(4-Fluorophenyl)acetohydrazideHCID 66860755HCID 66860755, compound

Product 1

HCID 1785271405-(1,1-dioxothiazinan-2-yl)-7-[5-[(4-fluorophenyl)methyl]-4H-1,2,4-triazol-3-yl]-1,6-naphthyridin-8-ol

Procedure

The title compound was prepared in a similar manner to that described in example 3 from 5-(1,1-dioxido-1,2-thiazinan-2-yl)-8-hydroxy-1,6-naphthyridine-7-carbonitrile (12 mg, 0.04 mmol) and 2-(4-fluorophenyl)acetic hydrazide (33 mg, 0.20 mmol) to give a white solid (6 mg, 31%). 1H NMR (CDCl3/CD3OD): δ 9.13 (m, 1 H), 8.56 (d, J=8.4 Hz, 1 H), 7.63 (dd, J=8.4, 4.0 Hz, 1 H), 7.32 (dd, J=8.4, 5.6 Hz, 2 H), 6.99 (t, J=8.4 Hz, 2 H), 4.17 (s, 2 H), 3.90 (m, 1 H), 3.77 (m, 1 H), 3.52 (m, 1 H), 3.32 (m, 1 H), 2.44-1.89 (m, 4 H); 19F NMR (CDCl3/CD3OD): δ −116.86; MS m/z 455 (M+1).

Sources & evidence

ORD record
ord-e68b324acfd64ec1a73d67c037981827
Source dataset
uspto-grants-2010_10
Patent number
US07812016B2

Reaction notes

Loading…