3-Methylthio-6-(3-methoxybenzyl)-1,2,4-triazin-5-one → HCID 178490029, compound

HRID 1758707Notes

Reaction equation

CS[C:3]1[NH:8][C:7](=[O:9])[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[N:5][N:4]=1.[NH:19]([C:23]1[S:24][CH:25]=[C:26]([CH2:28][S:29][CH2:30][CH2:31][NH2:32])[N:27]=1)[C:20]([NH2:22])=[NH:21]>CN(C)C=O>[CH3:18][O:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[CH2:10][C:6]1[C:7](=[O:9])[NH:8][C:3]([NH:32][CH2:31][CH2:30][S:29][CH2:28][C:26]2[N:27]=[C:23]([NH:19][C:20]([NH2:22])=[NH:21])[S:24][CH:25]=2)=[N:4][N:5]=1

Participants

Conditions

Temperature: 135 °C

Procedure

A mixture of 3-methylthio-6-(3-methoxybenzyl)-1,2,4-triazin-5-one (1.0 g) and 2-guanidino-4-[(2-aminoethyl)thiomethyl]thiazole (0.924 g) was heated at 135° C. for 3 hours. The residue was dissolved in dimethyl formamide (20 ml) and the solution was allowed to stand at room temperature for 8 days. A yellow brown solid precipitated out of solution, and this was filtered off and dried in air, then purified using pressure assisted short bed column chromatography (Kieselgel 60) with chloroform/methanol/ammonia (s.g. 0.880) 8:2:0.3 v/v/v as eluant, to give 6-(3-methoxybenzyl)-3-[2-(2-guanidinothiazol-4-yl-methylthio)ethylamino]-1,2,4-triazin-5-one (0.1 g). The n.m.r. spectrum of the product in d4 acetic acid using tetramethylsilane as an internal standard (δ=0) had the following resonances (δ): 2.8 (2H, multiplet); 3.5 (2H, multiplet); 3.75 (5H, singlet); 3.9 (2H, singlet); 6.8-6.9 (4H, multiplet); 7.2 (1H, broad doublet).

Workup

customA yellow brown solid precipitated out of solution
filtrationthis was filtered off
customdried in air
custompurified

Sources & evidence

ORD record: ord-4a77e9e177fc459bb463ebab08cdcf54
Source dataset: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04374836

Reaction notes

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