Hydrogen Bromide → HCID 178522040, compound

HRID 1667419Notes

Reaction equation

HRID 1667419 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([O:22]C)=[N:17][N:16]=[C:15]3[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1.Br>O1CCOCC1>[F:30][C:2]([F:1])([F:31])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([OH:22])=[N:17][N:16]=[C:15]3[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 67416694HCID 67416694, compound

Product 1

HCID 178522040HCID 178522040, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 1-methoxy-4-pyridin-2-yl-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (57 mg, 0.134 mmol), dioxane (3 mL) and 48% HBr (4 mL) was stirred at 40° C. for 1.5 hours. Concentration followed by chromatography (Hex/EtOAc) afforded 1-hydroxy-4-pyridin-2-yl-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (56 mg) as a white solid, 1H NMR (400 MHz, 4:1 CDCl3:d6-DMSO) δ: 7.27 (d, 1H), 7.36-7.44 (m, 2H), 7.90-7.95 (m, 2H), 8.05 (s, 1H), 8.21 (s, 1H), 8.33 (dd, 1H), 8.47 (d, 1H), 8.65 (dd, 1H), 8.81 (d, 1H), 10.50 (s, 1H), 12.80 (s, 1H) ppm. m/z 410.96.

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-59eb8884bc23444689966942ea8afb65
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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