Nicotinic acid, hydrazide → HCID 71699929, compound

HRID 456173Notes

Reaction equation

HRID 456173 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:33][NH2:34])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1>>[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:34]/[NH:33][C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=3)/[CH3:23])[N:20]=2)[N:15]=[N:14]1

Participants

3

Reactant 2

HCID 11112Nicotinic acid, hydrazideHCID 581905781-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone

Product 1

HCID 71699929HCID 71699929, compoundYield 64.2%

Procedure

The title compound (17.0 mg, 59%) was synthesized from 1-[3-(7-fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone (20.0 mg, 0.06 mmol) and nicotinic acid hydrazide (17.0 mg, 0.12 mmol) using the same procedure as described in the synthesis of example 72. 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.64, 11.38 (bs, 1H), 9.52 (s, 1H), 9.05 (s, 1H), 8.93 (dd, 1H), 8.78 (d, 1H), 8.42 (d, 1H), 8.20 (d, 1H), 7.84 (d, 1H), 7.56 (m, 2H), 6.26 (s, 2H), 2.49 (s, 3H). LCMS (method A): [MH]+=442, tR=2.10 min.

Workup

  1. customas described in the synthesis of example 72

Sources & evidence

ORD record
ord-de9d104845094855ad7cb80c91226ad7
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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