Semicarbazide hydrochloride → HCID 50898365, compound

HRID 456168Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][N:13]1[C:21]2[C:16](=[N:17][CH:18]=[C:19]([C:22](=O)[CH3:23])[N:20]=2)[N:15]=[N:14]1.Cl.[NH:26]([C:28]([NH2:30])=[O:29])[NH2:27]>CO>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][N:13]1[C:21]2=[N:20][C:19](/[C:22](=[N:27]/[NH:26][C:28]([NH2:30])=[O:29])/[CH3:23])=[CH:18][N:17]=[C:16]2[N:15]=[N:14]1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 1-[3-(7-fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone (30.0 mg, 0.09 mmol) in MeOH (10 mL), was added hydrazinecarboxamide hydrochloride (31.0 mg, 0.28 mmol). The mixture was heated at 45° C. and stirred overnight. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography with gradient (DCM:MeOH=10:1) to give the title compound as a white solid (25.0 mg, 67%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.91 (s, 1H), 9.85 (s, 1H), 8.93 (dd, 1H), 8.42 (d, 1H), 8.185 (d, 1H), 7.83 (d, 1H), 7.54 (dd, 1H), 6.20 (s, 2H), 2.28 (s, 3H). LCMS (method A): [MH]+=380, tR=1.98 min.

Workup

customThe solvent was removed under reduced pressure
customThe residue was purified by silica gel column chromatography with gradient (DCM:MeOH=10:1)

Sources & evidence

ORD record: ord-c6438a09386e49b297660b9192f670af
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497368B2

Reaction notes

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