1-(1-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone → (E)-N-[(3R)-pyrrolidin-3-yl]oxy-1-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyrazin-5-yl]ethanimine

HRID 1892362Notes

Reaction equation

HRID 1892362 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.Cl.Cl.[NH:26]1[CH2:30][CH2:29][C@@H:28]([O:31][NH2:32])[CH2:27]1>>[NH:26]1[CH2:30][CH2:29][C@@H:28]([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])[CH2:27]1

Participants

3

Reactant 2

HCID 593418021-(1-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanoneHCID 667139183(R)-Pyrrolidinyloxyamine dihydrochloride

Product 1

HCID 88004949(E)-N-[(3R)-pyrrolidin-3-yl]oxy-1-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyrazin-5-yl]ethanimineYield 60%

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) (25 mg, 0.082 mmol) and (R)—O-(pyrrolidin-3-yl)hydroxylamine dihydrochloride in 60% yield using the same procedure as described in the synthesis of example 22. 1H-NMR (400 MHz, CDCl3) δ ppm 9.41 (s, 1H), 8.92 (d, 1H), 8.13 (d, 1H), 8.09 (d, 1H), 7.91 (s, 1H), 7.82 (d, 1H), 7.41 (dd, 1H), 6.10 (s, 2H), 5.30 (s, 1H), 5.09 (s, 1H), 3.31 (m, 3H), 2.38 (s, 3H), 2.25 (m, 2H). LCMS (method B): [MH]+=389, tR=1.17 min.

Workup

  1. customas described in the synthesis of example 22

Sources & evidence

ORD record
ord-0514293794524d47a9e681d620d73955
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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