Cysteamine → 3-{2-[(2-Dimethylaminomethyl-4-thiazolyl)methylthio]ethylamino}-4-methylamino-1,2,5-thiadiazole 1-oxide

HRID 1702276Notes

Reaction equation

HRID 1702276 reaction equation
[CH3:1][NH:2][C:3]1[C:7](CCS)=[N:6][S:5](=[O:11])[N:4]=1.COC1C(OC)=NS(=O)N=1.[NH2:22][CH2:23][CH2:24][SH:25].CN.[CH3:28][N:29]([CH2:31][C:32]1[S:33][CH:34]=[C:35]([CH2:37]O)[N:36]=1)[CH3:30]>>[CH3:28][N:29]([CH2:31][C:32]1[S:33][CH:34]=[C:35]([CH2:37][S:25][CH2:24][CH2:23][NH:22][C:7]2[C:3]([NH:2][CH3:1])=[N:4][S:5](=[O:11])[N:6]=2)[N:36]=1)[CH3:30]

Participants

6

Reactant 5

HCID 6058CysteamineHCID 6329MethylamineHCID 1838020(2-((Dimethylamino)methyl)thiazol-4-yl)methanolHCID 129139473,4-Dimethoxy-1,2,5-thiadiazole 1-oxideHCID 204020743-Methylamino-4-(2-mercaptoethyl)-1,2,5-thiadiazole 1-oxide

Product 1

HCID 159641463-{2-[(2-Dimethylaminomethyl-4-thiazolyl)methylthio]ethylamino}-4-methylamino-1,2,5-thiadiazole 1-oxide

Procedure

Reaction of 3-methylamino-4-(2-mercaptoethyl)-1,2,5-thiadiazole 1-oxide [prepared by reacting 3,4-dimethoxy-1,2,5-thiadiazole 1-oxide with 2-aminoethanethiol and methylamine according to the procedure described in Example 25, Step A] with about one equivalent of 2-dimethylaminomethyl-4-hydroxymethylthiazole [prepared in Example 34, Step D], produces the title compound.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-f9a698caa6af468b91d6ce24843ac9f7
Source dataset
uspto-grants-1983_04
Patent number
US04380638

Reaction notes

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