O-Methylhydroxylamine → HCID 58190531, compound

HRID 1892379Notes

Reaction equation

HRID 1892379 reaction equation
[N:1]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][N:13]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:24][O:25][NH2:26]>CO>[CH3:24][O:25]/[N:26]=[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:1]=[CH:2][CH:3]=[CH:4]4)=[N:13][N:14]=2)[N:17]=1)\[CH3:22]

Participants

4

Reactant 2

HCID 4113O-MethylhydroxylamineHCID 581904611-(3-(Quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Product 1

HCID 58190531HCID 58190531, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (60 mg, 0.198 mmol) and O-methylhydroxylamine (49.6 mg, 0.593 mmol) in MeOH (10 mL) was stirred at rt overnight. Solvent was evaporated and the crude was purified by HPLC (acidic with 0.05% TFA and then neutralized to free base) to give 40 mg (60.8%) of the title compound as a white solid. 1H-NMR (400 MHz, MeOH-d4 δ ppm 8.82 (s, 1H), 8.32 (d, 1H), 8.12 (d, 1H), 7.98 (m, 3H), 7.84 (d, 1H), 7.54 (m, 1H), 4.83 (s, 2H), 4.09 (s, 3H), 2.28 (s, 3H). LC-MS (method B): [MH]+=333.1, tR=2.34 min.

Workup

  1. customSolvent was evaporated
  2. customthe crude was purified by HPLC (acidic with 0.05% TFA

Sources & evidence

ORD record
ord-e5df49391bc54c3e97428f1aa07ff835
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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