Isoniazid → HCID 50915994, compound

HRID 456170Notes

Reaction equation

HRID 456170 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][N:29]=[CH: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][N:29]=[CH:28][CH:27]=3)/[CH3:23])[N:20]=2)[N:15]=[N:14]1

Participants

3

Reactant 2

HCID 3767IsoniazidHCID 581905781-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone

Product 1

HCID 50915994HCID 50915994, compoundYield 70.2%

Procedure

The title compound (27.9 mg, 64%) 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 isonicotinic acid hydrazide (38.3 mg, 0.28 mmol) using the same procedure as described in the synthesis of example 72. 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.75, 11.39 (bs, 1H), 9.51 (s, 1H), 8.93 (dd, 1H), 8.79 (m, 2H), 8.42 (d, 1H), 8.20 (d, 1H), 7.836 (m, 3H), 7.54 (dd, 1H), 6.25 (s, 2H), 2.49 (s, 3H). LCMS (method E): [MH]+=442, tR=4.59 min.

Workup

  1. customas described in the synthesis of example 72

Sources & evidence

ORD record
ord-5735b38007194fb48ffb32dde2fb5ac2
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

Loading…