Ethanol, 2-(aminooxy)-, hydrochloride → 2-[(E)-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyrazin-5-yl]methylideneamino]oxyethanol

HRID 1892367Notes

Reaction equation

HRID 1892367 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([CH:21]=O)=[CH:19][N:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[NH2:24][O:25][CH2:26][CH2:27][OH:28]>>[OH:28][CH2:27][CH2:26][O:25]/[N:24]=[CH:21]/[C:18]1[N:17]=[C:16]2[N: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][C:15]2=[N:20][CH:19]=1

Participants

3

Reactant 2

HCID 22507086Ethanol, 2-(aminooxy)-, hydrochlorideHCID 866520351-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine-6-carbaldehyde

Product 1

HCID 581906132-[(E)-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyrazin-5-yl]methylideneamino]oxyethanolYield 45%

Procedure

The title compound was prepared from 1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine-6-carbaldehyde and 2-(aminooxy)ethanol hydrochloride in 45% yield using the same procedure as described in the synthesis of example 22. 1H-NMR (400 MHz, CD3OD), δ ppm 9.27 (s, 1H), 8.84 (m, 1H), 8.36 (s, 1H), 8.34 (d, 1H), 8.01 (d, 1H), 8.00 (s, 1H), 7.85 (d, 1H), 7.53 (dd, 1H), 6.20 (s, 2H), 4.39 (t, 2H), 3.87 (t, 2H). LCMS (method B): [MH]+=350, tR=1.94 min.

Workup

  1. customas described in the synthesis of example 22

Sources & evidence

ORD record
ord-8d12528a9b384b6294c308253eefa830
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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