Semicarbazide hydrochloride → HCID 71699895, compound

HRID 456098Notes

Reaction equation

HRID 456098 reaction equation
[F:1][C:2]([F:25])([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:3]1[N:7]2[N:8]=[C:9]([C:12](=O)[CH3:13])[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.Cl.[NH:27]([C:29]([NH2:31])=[O:30])[NH2:28]>CO>[F:1][C:2]([F:25])([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:3]1[N:7]2[N:8]=[C:9](/[C:12](=[N:28]/[NH:27][C:29]([NH2:31])=[O:30])/[CH3:13])[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1

Participants

4

Reactant 2

HCID 11236Semicarbazide hydrochlorideHCID 581904681-(3-(Difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Product 1

HCID 71699895HCID 71699895, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(3-(difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (100 mg, 0.295 mmol) and hydrazinecarboxamide hydrochloride (44.3 mg, 0.589 mmol) in MeOH was stirred at room temperature for overnight. Solvent was evaporated and the residue was dissolved in a small amount of MeOH. Solid was filtered and dried to give the title compound as a white solid (90 mg, 75%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.90 (s, 1H), 9.06 (d, 1H), 8.62 (d, 1H), 8.49 (m, 2H), 8.34 (d, 1H), 8.20 (d, 1H), 8.03 (d, 1H), 7.70 (m, 1H), 6.82 (broad, 2H), 2.07 (s, 3H). LCMS (method B): [MH]+=397.1, tR=2.08 min.

Workup

  1. customSolvent was evaporated
  2. dissolutionthe residue was dissolved in a small amount of MeOH
  3. filtrationSolid was filtered
  4. customdried

Sources & evidence

ORD record
ord-9840ba86a49847e2a13f26c4afb4d803
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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