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

HRID 1959706Notes

Reaction equation

HRID 1959706 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), 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-0ff7097aff9d4b99853ddbc8e8963160
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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