O-((4-Methoxyphenyl)methyl)hydroxylamine → HCID 58190475, compound

HRID 1959694Notes

Reaction equation

HRID 1959694 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]([C:21](=O)[CH3:22])=[CH:19][N:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:29]([CH2:30][O:31][NH2:32])=[CH:28][CH:27]=1>>[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:29]([CH2:30][O:31]/[N:32]=[C:21](/[C:18]2[N:17]=[C:16]3[N:12]([CH2:11][C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N:1]=[CH:2][CH:3]=[CH:4]5)[N:13]=[N:14][C:15]3=[N:20][CH:19]=2)\[CH3:22])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 120426O-((4-Methoxyphenyl)methyl)hydroxylamine2×HCID 593418021-(1-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone

Product 1

HCID 58190475HCID 58190475, compoundYield 37%

Procedure

The title compound was prepared from 1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone (22.4) and O-(4-methoxybenzyl)hydroxylamine (intermediate G) in 37% yield using the same procedure as described in the synthesis of example 22. 1H-NMR (400 MHz, CDCl3), δ ppm 9.44 (s, 1H), 8.93 (s, 1H), 8.13 (m, 2H), 7.91 (s, 1H), 7.84 (d, 1H), 7.47 (dd, 1H), 7.44 (d, 2H), 6.92 (d, 2H), 6.10 (s, 2H), 5.28 (s, 2H), 3.82 (s, 3H), 2.37 (s, 3H). LCMS (method A): [MH]+=440, tR=5.94 min.

Workup

  1. customas described in the synthesis of example 22

Sources & evidence

ORD record
ord-55bab8d7e6ed472c81df48ec08eea78d
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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