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 1959700Notes

Reaction equation

HRID 1959700 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-bdf3fdace9bb4804aa7efde67eef2150
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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