O-ethylhydroxylamine hydrochloride → (E)-N-ethoxy-1-[3-(1-quinolin-6-ylcyclopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethanimine

HRID 1892408Notes

Reaction equation

HRID 1892408 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3([C:14]4[N:18]5[N:19]=[C:20]([C:23](=O)[CH3:24])[CH:21]=[CH:22][C:17]5=[N:16][N:15]=4)[CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[CH2:27]([O:29][NH2:30])[CH3:28]>C(Cl)Cl>[CH2:27]([O:29]/[N:30]=[C:23](/[C:20]1[CH:21]=[CH:22][C:17]2[N:18]([C:14]([C:11]3([C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N:1]=[CH:2][CH:3]=[CH:4]5)[CH2:13][CH2:12]3)=[N:15][N:16]=2)[N:19]=1)\[CH3:24])[CH3:28]

Participants

4

Reactant 2

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 581905101-(3-(1-(Quinolin-6-yl)cyclopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Product 1

HCID 50991538(E)-N-ethoxy-1-[3-(1-quinolin-6-ylcyclopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethanimine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(3-(1-(quinolin-6-yl)cyclopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (30 mg, 0.09 mmol) and O-ethyl-hydroxylamine hydrochloride (18 mg, 0.18 mmol) in 2 mL of DCM was stirred at 40° C. overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with EtOAc/methanol gradient to afford the title compound. 1H-NMR (400 MHz, CDCl3) 3 ppm 8.84 (d, 1H), 8.29 (d, 1H), 8.25 (d, 1H), 7.92-7.91 (m, 2H), 7.72-7.68 (m, 2H), 7.49 (dd, 1H), 4.26 (q, 2H), 2.01 (s, 3H), 1.76 (s, 2H), 1.66 (s, 2H), 1.27 (t, 3H). LCMS (method A): [MH]+=373, tR=5.56 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel eluting with EtOAc/methanol gradient

Sources & evidence

ORD record
ord-30cec5a60cdd4a12b0e021566808d770
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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