Hydrochloric Acid → 2-[(E)-1-[3-[3-(4-methylpiperazin-1-yl)quinolin-6-yl]sulfanyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]ethylideneamino]oxyethanol

HRID 2175161Notes

Reaction equation

HRID 2175161 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[N:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([S:18][C:19]2[N:23]4[CH:24]=[C:25]([C:28](=O)[CH3:29])[CH:26]=[CH:27][C:22]4=[N:21][N:20]=2)=[CH:13][CH:12]=3)[CH2:4][CH2:3]1.[NH2:31][O:32][CH2:33][CH2:34][OH:35].Cl>CO>[OH:35][CH2:34][CH2:33][O:32]/[N:31]=[C:28](/[C:25]1[CH:26]=[CH:27][C:22]2[N:23]([C:19]([S:18][C:14]3[CH:15]=[C:16]4[C:11](=[CH:12][CH:13]=3)[N:10]=[CH:9][C:8]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:17]4)=[N:20][N:21]=2)[CH:24]=1)\[CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3014186Ethanol, 2-(aminooxy)-HCID 866962941-(3-(3-(4-Methylpiperazin-1-yl)quinolin-6-ylthio)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethanone

Product 1

HCID 715372062-[(E)-1-[3-[3-(4-methylpiperazin-1-yl)quinolin-6-yl]sulfanyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]ethylideneamino]oxyethanolYield 15%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (86.2) (120 mg, 0.287 mmol) and 2-(aminooxy)ethanol (44.2 mg, 0.573 mmol) in MeOH (10 ml) was added drops of HCl (3 N) to reach pH about 5 and then stirred at rt for overnight. Solvent was evaporated and the residue was purified by preparative base HPLC (gradient eluent NB from 20/80 to 95/5. mobile phase A: NH4OH/CH3CN 0.05%; mobile phase B: NH4OH/H2O 0.05%) to afford the title compound (20 mg, yield 15%).

Workup

  1. customSolvent was evaporated
  2. customthe residue was purified by preparative base HPLC (gradient eluent NB from 20/80 to 95/5. mobile phase A: NH4OH/CH3CN 0.05%; mobile phase B: NH4OH/H2O 0.05%)

Sources & evidence

ORD record
ord-6076afd0dc924ad3a7a8750a375348df
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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