Ethanol, 2-(aminooxy)- → 2-[(E)-1-[3-[(4,6-difluoro-1-methylindazol-5-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]oxyethanol

HRID 1892396Notes

Reaction equation

HRID 1892396 reaction equation
[F:1][C:2]1[C:10]([CH2:11][C:12]2[N:16]3[N:17]=[C:18]([C:21](=O)[CH3:22])[CH:19]=[CH:20][C:15]3=[N:14][CH:13]=2)=[C:9]([F:24])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH3:25].[NH2:26][O:27][CH2:28][CH2:29][OH:30]>CO.C(Cl)Cl>[OH:30][CH2:29][CH2:28][O:27]/[N:26]=[C:21](/[C:18]1[CH:19]=[CH:20][C:15]2[N:16]([C:12]([CH2:11][C:10]3[C:2]([F:1])=[C:3]4[C:7](=[CH:8][C:9]=3[F:24])[N:6]([CH3:25])[N:5]=[CH:4]4)=[CH:13][N:14]=2)[N:17]=1)\[CH3:22]

Participants

5

Reactant 2

HCID 3014186Ethanol, 2-(aminooxy)-2×HCID 581904931-(3-((4,6-Difluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone

Product 1

HCID 581905322-[(E)-1-[3-[(4,6-difluoro-1-methylindazol-5-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]oxyethanolYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(3-((4,6-difluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone (62 mg, 0.136 mmol) and 2-(aminooxy)ethanol (intermediate S) (77 mg, 0.681 mmol) in 3 mL of MeOH and 2 mL of DCM was stirred at rt for 2 days. Solvent was evaporated to give a residue, which was purified by chromatography (DCM:MeOH 10:1) and recrystallized from MeOH to give the title compound as a white solid (32 mg, 59%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.16 (s, 1H), 8.04 (d, 1H), 7.62 (t, 2H), 7.48 (d, 1H), 4.44 (s, 2H), 4.24 (t, 2H), 4.00 (s, 3H), 3.68 (m, 2H), 2.29 (s, 3H). LCMS (method E): [MH]+=401.1, tR=5.591 min.

Workup

  1. customSolvent was evaporated
  2. customto give a residue, which
  3. customwas purified by chromatography (DCM:MeOH 10:1)
  4. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-819176359c72486e849c3487c9af8473
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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