Hydroxylamine, O-ethyl- → HCID 58190492, compound

HRID 1892380Notes

Reaction equation

HRID 1892380 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.[CH2:24]([O:26][NH2:27])[CH3:25]>CO>[CH2:24]([O:26]/[N:27]=[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])[CH3:25]

Participants

4

Reactant 2

HCID 69357Hydroxylamine, O-ethyl-HCID 581904611-(3-(Quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Product 1

HCID 58190492HCID 58190492, compoundYield 46.1%

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 (41.2) (30 mg, 0.099 mmol) and O-ethylhydroxylamine (18.12 mg, 0.297 mmol) in 5 mL of MeOH was stirred at rt overnight. Solvent was evaporated and the crude was purified by HPLC (acidic with 0.05% TFA) to give 15.8 mg (46.1%) of the title compound as a white TFA salt. 1H-NMR (400 MHz, MeOH-d4 δ ppm 9.05 (s, 1H), 8.85 (d, 1H), 8.23 (s, 1H), 8.12 (m, 3H), 7.98 (d, 1H), 7.89 (m, 1H), 4.91 (s, 2H), 4.36 (q, 2H), 2.30 (s, 3H), 1.36 (t, 3H). LC-MS (method B): [MH]+=347.1.1, tR=2.50 min.

Workup

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

Sources & evidence

ORD record
ord-5ec2778233c649bca17675404bf9c328
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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