Pyridine → 2-(7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-on-6-yl)-4,5,6,7-tetrahydro-1,2,3-benzotriazole-1-oxide

HRID 476512Notes

Reaction equation

[F:1][C:2]1[C:15]([NH:16][NH:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]2=[N:24][OH:25])=[CH:14][C:5]2[N:6]([CH2:11][C:12]#[CH:13])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.N1C=CC=CC=1>O1CCCC1.O.S([O-])([O-])(=O)=O.[Cu+2]>[F:1][C:2]1[C:15]([N:16]2[N+:24]([O-:25])=[C:19]3[CH2:20][CH2:21][CH2:22][CH2:23][C:18]3=[N:17]2)=[CH:14][C:5]2[N:6]([CH2:11][C:12]#[CH:13])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-[2-(7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-on-6-yl)hydrazino]cyclohexanone oxime (0.4 g) in tetrahydrofuran (6 ml), 15% aqueous pyridine (7 g) was added, and a solution of copper sulfate (0.7 g) in water (1.5 ml) was added thereto, followed by heating at 80° C. for 2 hours. The reaction mixture was allowed to cool, combined with water and extracted with ethyl acetate. The organic layer was washed with 10% aqueous copper sulfate solution, dried and concentrated. The residue was purified by silica gel column chromatography using ethyl acetate as an eluent to give Compound No. 1 (0.2 g). m.p., 186°-187° C.

Workup

temperatureto cool
extractionextracted with ethyl acetate
washThe organic layer was washed with 10% aqueous copper sulfate solution
customdried
concentrationconcentrated
customThe residue was purified by silica gel column chromatography
customto give Compound No
customm.p., 186°-187° C.

Sources & evidence

ORD record: ord-542bd86611a448529b031e8b1afeaf4c
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04885024

Reaction notes

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