Hydrogen Bromide → HCID 54713250, compound

HRID 1453881Notes

Reaction equation

[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:24]([O:25]C)=[C:13]3[C:14](=[O:23])[N:15]([CH3:22])[C:16]4[C:21]([N:12]3[N:11]=2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[O:9])=[CH:4][CH:3]=1.Br>CC(O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:24]([OH:25])=[C:13]3[C:14](=[O:23])[N:15]([CH3:22])[C:16]4[C:21]([N:12]3[N:11]=2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[O:9])=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-(4-fluorobenzyl)-3-methoxy-5-methyl-4-oxo-4,5-dihydropyrazolo[1,5-a]quinoxaline-2-carboxamide (85 mg, 0.22 mmol) in AcOH (1 mL) was added 30% HBr in AcOH (2 mL). The mixture was stirred and warmed to 50° C. for 8 hours. The solvent was removed under reduced pressure. The residue was triturated in AcOH to give the title compound as a white solid. 1H NMR (400 MHz, d6-DMSO) δ 9.82 (br s, 1H), 9.06 (t, J=6.0 Hz, 1H), 8.20 (d, J=8.0 Hz, 1H), 7.58 (d, J=7.8 Hz, 1H), 7.51 (t, J=7.8 Hz, 1H), 7.38-7.43 (m, 3H), 7.17 (t, J=9.0 Hz, 2H), 4.50 (d, J=6.2 Hz, 2H), 4.02 (s, 3H), 3.57 (s, 3H); ES MS (M+1)=367.

Workup

customThe solvent was removed under reduced pressure
customThe residue was triturated in AcOH

Sources & evidence

ORD record: ord-bfaf887605984e6fbcddf9ed24ff3a27
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07476666B2

Reaction notes

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