Ethanol, 2-(aminooxy)- → HCID 50991634, compound

HRID 1892387Notes

Reaction equation

HRID 1892387 reaction equation
[F:1][C:2]([F:25])([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:3]1[N:7]2[N:8]=[C:9]([C:12](=O)[CH3:13])[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.[NH2:26][O:27][CH2:28][CH2:29][OH:30]>CO>[OH:30][CH2:29][CH2:28][O:27]/[N:26]=[C:12](/[C:9]1[CH:10]=[CH:11][C:6]2[N:7]([C:3]([C:2]([F:25])([F:1])[C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[N:21]=[CH:20][CH:19]=[CH:18]4)=[N:4][N:5]=2)[N:8]=1)\[CH3:13]

Participants

4

Reactant 2

HCID 3014186Ethanol, 2-(aminooxy)-2×HCID 581904681-(3-(Difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Product 1

HCID 50991634HCID 50991634, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(3-(difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (54 mg, 0.159 mmol) and 2-(aminooxy)ethanol (intermediate S) (36.1 mg, 0.318 mmol) in 8 mL of MeOH was stirred at it overnight. Solvent was evaporated and the residue was partitioned between water and EtOAc. Aqueous layer was extracted with EtOAc twice. Organic layers were combined, washed with brine and dried over Na2SO4. Solvent was evaporated and the crude was purified by HPLC (basic with 0.05% NH4OH) to give 35 mg (55%) of the title compound as a white solid. 1H-NMR (400 MHz, MeOH-d4) δ ppm 8.98 (d, 1H), 8.52 (d, 1H), 8.43 (s, 1H), 8.23 (d, 1H), 8.19 (d, 1H), 8.06 (d, 1H), 8.04 (d, 1H), 7.66 (m, 1H), 4.36 (m, 2H), 3.84 (m, 2H), 2.18 (s, 3H). LCMS (method B): [MH]+=398.9, tR=2.29 min.

Workup

  1. customSolvent was evaporated
  2. customthe residue was partitioned between water and EtOAc
  3. extractionAqueous layer was extracted with EtOAc twice
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customSolvent was evaporated
  7. customthe crude was purified by HPLC (basic with 0.05% NH4OH)

Sources & evidence

ORD record
ord-83462306c9be47ffba1b74e5f376ebf1
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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