Hydroxyamine hydrochloride → (NE)-N-[1-[3-[1-(5,7-difluoroquinolin-6-yl)ethyl]triazolo[4,5-b]pyrazin-5-yl]ethylidene]hydroxylamine

HRID 1892440Notes

Reaction equation

HRID 1892440 reaction equation
[F:1][C:2]1[C:11]([CH:12]([N:14]2[C:18]3=[N:19][C:20]([C:23](=O)[CH3:24])=[CH:21][N:22]=[C:17]3[N:16]=[N:15]2)[CH3:13])=[C:10]([F:26])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.Cl.[NH2:28][OH:29]>>[F:1][C:2]1[C:11]([CH:12]([N:14]2[C:18]3=[N:19][C:20](/[C:23](=[N:28]/[OH:29])/[CH3:24])=[CH:21][N:22]=[C:17]3[N:16]=[N:15]2)[CH3:13])=[C:10]([F:26])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

3

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 581905541-(1-(1-(5,7-Difluoroquinolin-6-yl)ethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone

Product 1

HCID 136062023(NE)-N-[1-[3-[1-(5,7-difluoroquinolin-6-yl)ethyl]triazolo[4,5-b]pyrazin-5-yl]ethylidene]hydroxylamineYield 65%

Procedure

The title compound (26.4 mg, 63%) was synthesized from 1-(1-(1-(5,7-difluoroquinolin-6-yl)ethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone (73.7) (40.0 mg, 0.11 mmol) and hydroxylamine hydrochloride (15.7 mg, 0.23 mmol) using the same procedure as described in the synthesis of example 73. 1H-NMR (400 MHz, DMSO-d6) δ ppm 12.28 (bs, 1H), 9.23 (s, 1H), 9.01 (d, 1H), 8.52 (d, 1H), 7.73 (d, 1H), 7.63 (dd, 1H), 6.80 (q, 1H), 2.36 (d, 3H), 2.05 (s, 3H). LCMS (method A): [MH]+=370, tR=5.53 min.

Workup

  1. customas described in the synthesis of example 73

Sources & evidence

ORD record
ord-637e4056cf1a43d7b0bfb4f95b0f9484
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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