Semicarbazide hydrochloride → [(E)-1-[3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]urea

HRID 456103Notes

Reaction equation

HRID 456103 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]3[N:16]4[N:17]=[C:18]([C:21](=O)[CH3:22])[CH:19]=[CH:20][C:15]4=[N:14][N:13]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[NH:25]([C:27]([NH2:29])=[O:28])[NH2:26]>CO>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]3[N:16]4[N:17]=[C:18](/[C:21](=[N:26]/[NH:25][C:27]([NH2:29])=[O:28])/[CH3:22])[CH:19]=[CH:20][C:15]4=[N:14][N:13]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 11236Semicarbazide hydrochlorideHCID 581904611-(3-(Quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Product 1

HCID 71699899[(E)-1-[3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]ureaYield 84.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (35 mg, 0.115 mmol) and hydrazinecarboxamide hydrochloride (17.32 mg, 0.231 mmol) in MeOH was stirred at room temperature for overnight. Solid was filtered and dried to provide the title compound as a light yellow solid (35 mg, 84%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.90 (s, 1H), 9.10 (d, 1H), 8.79 (d, 1H), 8.37 (d, 1H), 8.17 (m, 3H), 8.03 (d, 1H), 7.83 (m, 1H), 6.85 (broad, 2H), 4.84 (s, 2H), 2.24 (s, 3H). LCMS (method A): [MH]+=361.1, tR=3.58 min.

Workup

  1. filtrationSolid was filtered
  2. customdried

Sources & evidence

ORD record
ord-561bffe908694059a0fe71276f349789
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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