Triethylamine → HCID 71699889, compound

HRID 456085Notes

Reaction equation

HRID 456085 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[C:12]([C:15]1[N:19]2[N:20]=[C:21]([C:24](=O)[CH3:25])[CH:22]=[CH:23][C:18]2=[N:17][CH:16]=1)([OH:14])[CH3:13].Cl.[NH2:28][NH:29][C:30]([NH2:32])=[O:31].C(N(CC)CC)C>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[C:12]([C:15]1[N:19]2[N:20]=[C:21](/[C:24](=[N:28]/[NH:29][C:30]([NH2:32])=[O:31])/[CH3:25])[CH:22]=[CH:23][C:18]2=[N:17][CH:16]=1)([OH:14])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11236Semicarbazide hydrochlorideHCID 669270341-(3-(1-(7-Fluoroquinolin-6-yl)-1-hydroxyethyl)imidazo[1,2-b]pyridazin-6-yl)ethanone

Product 1

HCID 71699889HCID 71699889, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(3-(1-(7-fluoroquinolin-6-yl)-1-hydroxyethyl)imidazo[1,2-b]pyridazin-6-yl)ethanone (35 mg, 0.09 mmol) in methanol (20 mL) was added semicarbazide hydrochloride (20 mg, 0.18 mmol). Triethyl amine was added dropwise to adjust the pH to 5-6. The reaction mixture was stirred at room temperature overnight. The solution was concentrated in reduced pressure and the residue was purified by column chromatography (3%-50% MeOH in CH2Cl2) to afford 23 mg (yield: 62%) title compound. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.47 (s, 1H), 8.87 (d, 1H), 8.52 (m, 2H), 8.06 (d, 1H), 7.92 (d, 1H), 7.85 (s, 1H), 7.54 (m, 2H), 6.62 (b, 2H), 6.24 (s, 1H), 2.13 (s, 3H), 1.53 (s, 3H). LCMS (method A): [MH]+=408, tR=4.03 min.

Workup

  1. concentrationThe solution was concentrated in reduced pressure
  2. customthe residue was purified by column chromatography (3%-50% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-04d66a5b0d5b46228fa8a6a37313e73d
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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