Propionylhydrazine → N-[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyrazin-5-yl]ethylideneamino]propanamide

HRID 456172

Reaction equation

HRID 456172 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][N:13]1[C:21]2[C:16](=[N:17][CH:18]=[C:19]([C:22](=O)[CH3:23])[N:20]=2)[N:15]=[N:14]1.[C:25]([NH:29][NH2:30])(=[O:28])[CH2:26][CH3:27]>>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][N:13]1[C:21]2[C:16](=[N:17][CH:18]=[C:19](/[C:22](=[N:30]/[NH:29][C:25](=[O:28])[CH2:26][CH3:27])/[CH3:23])[N:20]=2)[N:15]=[N:14]1

Participants

3

Reactant 2

HCID 79890PropionylhydrazineHCID 581905781-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone

Product 1

HCID 71699928N-[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyrazin-5-yl]ethylideneamino]propanamideYield 80.7%

Procedure

The title compound (28.5 mg, 74%) was synthesized from 1-[3-(7-fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone (30.0 mg, 0.09 mmol) and propionic acid hydrazide (24.6 mg, 0.28 mmol) using the same procedure as described in the synthesis of example 72. 1H-NMR (400 MHz, DMSO-d6) δ ppm 10.93, 10.76 (bs, 1H), 9.45 (s, 1H), 8.92 (dd, 1H), 8.41 (d, 1H), 8.18 (d, 1H), 7.83 (d, 1H), 7.53 (dd, 1H), 6.22 (s, 2H), 2.79 (q, 2H), 2.31 (s, 3H), 1.09 (t, 3H). LCMS (method E): [MH]+=393, tR=4.78 min.

Workup

  1. customas described in the synthesis of example 72

Sources & evidence

ORD record
ord-e23f91f19a36456a818920b614f7b186
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Linked notes

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