Ethanol, 2-(aminooxy)-, hydrochloride → 2-[(E)-1-[3-[1-(1-methylindazol-5-yl)ethyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]oxyethanol

HRID 1959672Notes

Reaction equation

HRID 1959672 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([C:13]3[N:17]4[N:18]=[C:19]([C:22](=O)[CH3:23])[CH:20]=[CH:21][C:16]4=[N:15][CH:14]=3)[CH3:12])=[CH:8][CH:9]=2)[CH:4]=[N:3]1.Cl.[NH2:26][O:27][CH2:28][CH2:29][OH:30]>>[OH:30][CH2:29][CH2:28][O:27]/[N:26]=[C:22](/[C:19]1[CH:20]=[CH:21][C:16]2[N:17]([C:13]([CH:11]([C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[N:2]([CH3:1])[N:3]=[CH:4]4)[CH3:12])=[CH:14][N:15]=2)[N:18]=1)\[CH3:23]

Participants

3

Reactant 2

HCID 22507086Ethanol, 2-(aminooxy)-, hydrochlorideHCID 581904911-(3-(1-(1-Methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazin-6-yl)ethanone

Product 1

HCID 509914502-[(E)-1-[3-[1-(1-methylindazol-5-yl)ethyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]oxyethanolYield 18.3%

Procedure

The title compound (9.0 mg, 17%, 88% purity) was synthesized from 1-(3-(1-(1-methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazin-6-yl)ethanone (40.0 mg, 0.13 mmol) and 2-(aminooxy)ethanol hydrochloride (19.31 mg, 0.25 mmol) using the same procedure as described in the synthesis of example 13. 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.94 (d, 1H), 7.85 (s, 1H), 7.79 (s, 1H), 7.66 (s, 1H), 7.85 (d, 1H), 7.52 (d, 1H), 7.37 (dd, 1H), 4.72 (t, 2H), 4.21 (t, 2H), 3.97 (s, 3H), 3.66 (q, 1H), 2.20 (s, 3H), 1.78 (d, 3H). LCMS (method A): [MH]+=379, tR=5.25 min.

Workup

  1. customas described in the synthesis of example 13

Sources & evidence

ORD record
ord-1c648b3c10c647af9a42aec1f0669a5e
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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