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 1959733Notes

Reaction equation

HRID 1959733 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-a4bc65a88ed0461bb11c86e2d41e9c45
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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