Ethanol, 2-(aminooxy)-, hydrochloride → 2-[(E)-1-[3-[(1-methylindazol-5-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]oxyethanol

HRID 1959666Notes

Reaction equation

HRID 1959666 reaction equation
[CH3:1][N:2]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][CH:13]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1.Cl.[NH2:25][O:26][CH2:27][CH2:28][OH:29]>C1COCC1>[OH:29][CH2:28][CH2:27][O:26]/[N:25]=[C:21](/[C:18]1[CH:19]=[CH:20][C:15]2[N:16]([C:12]([CH2:11][C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[N:2]([CH3:1])[N:3]=[CH:4]4)=[CH:13][N:14]=2)[N:17]=1)\[CH3:22]

Participants

4

Reactant 2

HCID 22507086Ethanol, 2-(aminooxy)-, hydrochlorideHCID 581905161-(3-((1-Methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone

Product 1

HCID 581905252-[(E)-1-[3-[(1-methylindazol-5-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]oxyethanolYield 58.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(3-((1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone (20.0 mg, 0.07 mmol) and 2-(aminooxy)ethanol hydrochloride (14.87 mg, 0.13 mmol) in 10 mL THF was stirred at 40° C. overnight. Solvent was removed in vacuo. The crude product was purified on flash chromatography (DCM:MeOH=50:1) to give the title compound as a yellow solid (15.0 mg, 57%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.04 (d, 1H), 7.94 (s, 1H), 7.68˜7.61 (m, 3H), 7.54 (d, 1H), 7.39 (d, 1H), 4.41 (s, 2H), 4.23 (s, 2H), 3.98 (s, 3H), 3.68 (s, 2H), 2.29 (s, 3H). LCMS (method A): [MH]+=365, tR=4.70 min.

Workup

  1. customSolvent was removed in vacuo
  2. customThe crude product was purified on flash chromatography (DCM:MeOH=50:1)

Sources & evidence

ORD record
ord-a56a1271bb5544f3998387c0f263df6c
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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