O-3-oxetanyl-Hydroxylamine → HCID 58190528, compound

HRID 1959764Notes

Reaction equation

HRID 1959764 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.[O:24]1[CH2:27][CH:26]([O:28][NH2:29])[CH2:25]1>>[O:24]1[CH2:27][CH:26]([O:28]/[N:29]=[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])[CH2:25]1

Participants

3

Reactant 2

HCID 58190526O-3-oxetanyl-Hydroxylamine2×HCID 593418021-(1-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone

Product 1

HCID 58190528HCID 58190528, compoundYield 23%

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-(oxetan-3-yl)hydroxylamine (intermediate U) in 23% yield using the same procedure as described in the synthesis of example 22. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.27 (s, 1H), 8.89 (m, 1H), 8.35 (d, 1H), 8.01 (m, 2H), 7.82 (m, 1H), 7.52 (dd, 1H), 6.22 (s, 2H), 5.45 (t, 1H), 4.86 (t, 2H), 4.66 (m, 2H), 2.40 (s, 3H). LCMS (method B): [MH]+=376, tR=2.26 min.

Workup

  1. customas described in the synthesis of example 22

Sources & evidence

ORD record
ord-011fb2c9856f4f378e3739560c83ed7a
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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