2-Cyanobenzoic acid → HCID 11373089, compound

HRID 2356504Notes

Reaction equation

HRID 2356504 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O)#[N:2].[CH:12]1([CH2:15][CH2:16][NH:17][C:18]([C:20]2[N:21]=[N:22][C:23]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[CH:24][CH:25]=2)=[O:19])[CH2:14][CH2:13]1>>[CH:12]1([CH2:15][CH2:16][NH:17][C:18]([C:20]2[N:21]=[N:22][C:23]([N:26]3[CH2:31][CH2:30][N:29]([C:5](=[O:7])[C:4]4[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=4[C:1]#[N:2])[CH2:28][CH2:27]3)=[CH:24][CH:25]=2)=[O:19])[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 1380612-Cyanobenzoic acidHCID 66849327N-(2-cyclopropylethyl)-6-(1-piperazinyl)-3-pyridazinecarboxamide

Product 1

HCID 11373089HCID 11373089, compound

Procedure

Following the procedure of Example 9, making variations only as required to use 2-cyanobenzoic acid in place of 2,5-dichlorobenzoic acid to react with 6-piperazin-1-yl-pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide, the title compound was obtained as a white solid (25.8% yield). 1H NMR (300 MHz, CDCl3) δ 8.05, 7.97, 7.76-7.72, 7.69-7.66, 7.58-7.55, 7.53-7.43, 6.99, 4.3-3.94, 3.88-3.85, 3.58-3.51, 1.49, 0.78-0.65, 0.48-0.37, 0.16-0.02. 13C NMR (75 MHz, CDCl3) δ166.5, 162.8, 159.9, 145.3, 139.3, 133.3, 133.04, 129.9, 127.6, 127.03, 116.8, 112.4, 109.9, 46.4, 44.7, 44.6, 41.6, 39.6, 34.4, 8.6, 4.1. MS (ES+) m/z 405.2 (M+1).

Sources & evidence

ORD record
ord-ee4fda72b6fc4531a573cc34ae178d7f
Source dataset
uspto-grants-2010_07
Patent number
US07759348B2

Reaction notes

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