3-Methylthio-6-(3-pyridylmethyl)-1,2,4-triazin-5-one → HCID 178512707, compound

HRID 1758708Notes

Reaction equation

HRID 1758708 reaction equation
CS[C:3]1[NH:8][C:7](=[O:9])[C:6]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:5][N:4]=1.[NH:17]([C:21]1[S:22][CH:23]=[C:24]([CH2:26][S:27][CH2:28][CH2:29][NH2:30])[N:25]=1)[C:18]([NH2:20])=[NH:19]>>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][C:6]2[C:7](=[O:9])[NH:8][C:3]([NH:30][CH2:29][CH2:28][S:27][CH2:26][C:24]3[N:25]=[C:21]([NH:17][C:18]([NH2:20])=[NH:19])[S:22][CH:23]=3)=[N:4][N:5]=2)[CH:12]=1

Participants

3

Reactant 2

HCID 1357554243-Methylthio-6-(3-pyridylmethyl)-1,2,4-triazin-5-oneHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178512707HCID 178512707, compoundYield 19.5%

Conditions

Temperature
140 °C

Procedure

A mixture of 3-methylthio-6-(3-pyridylmethyl)-1,2,4-triazin-5-one (0.23 g) and 2-guanidino-4-[(2-aminoethyl)thiomethyl]thiazole (0.23 g) was heated at 140° C. for 2 hours and then allowed to cool to room temperature. The black solid mass was triturated with a mixture of methanol (10 ml) and dimethylformamide (2 ml) and the resulting pale brown solid was filtered off. This was purified by preparative TLC using Merck Kieselgel GF 254 2 mm preparative plates in chloroform/methanol/ammonia (s.g. 0.880) 8:2:0.3 v/v/v as eluant to give 6-(3-pyridylmethyl)-3-[2-(2-guanidinothiazol-4-ylmethylthio)-ethylamino]-1,2,4-triazin-5-one (0.08 g). The n.m.r. spectrum of the product in d6 dimethyl sulphoxide using tetramethylsilane as an internal standard (δ=0) had the following resonances: 2.7 (2H, triplet); 3.4 (2H, broad multiplet); 3.6 (2H, sharp singlet); 3.8-4.1 (8H, broad multiplet--contains H2O); 6.6 (1H, sharp singlet); 6.9 (4H, broad singlet); 7.3 (1H, multiplet); 7.7 (1H, double triplet); 8.5 (2H, multiplet).

Workup

  1. temperatureto cool to room temperature
  2. customThe black solid mass was triturated with a mixture of methanol (10 ml) and dimethylformamide (2 ml)
  3. filtrationthe resulting pale brown solid was filtered off
  4. customThis was purified by preparative TLC

Sources & evidence

ORD record
ord-d44b759c0b5b41cca3b99ffd9e1947d8
Source dataset
uspto-grants-1983_02
Patent number
US04374836

Reaction notes

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