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

HRID 1758638Notes

Reaction equation

HRID 1758638 reaction equation
[CH3:1][NH:2][C:3]1[C:7]([NH:8][CH2:9][CH2:10][SH:11])=[N:6][S:5](=[O:12])[N:4]=1.COC1C(OC)=NS(=O)N=1.NCCS.CN.[CH3:29][N:30]([CH2:32][C:33]1[S:34][CH:35]=[C:36]([CH2:38]O)[N:37]=1)[CH3:31]>>[CH3:29][N:30]([CH2:32][C:33]1[S:34][CH:35]=[C:36]([CH2:38][S:11][CH2:10][CH2:9][NH:8][C:7]2[C:3]([NH:2][CH3:1])=[N:4][S:5](=[O:12])[N:6]=2)[N:37]=1)[CH3:31]

Participants

6

Reactant 5

HCID 6058CysteamineHCID 6329MethylamineHCID 1838020(2-((Dimethylamino)methyl)thiazol-4-yl)methanolHCID 129139473,4-Dimethoxy-1,2,5-thiadiazole 1-oxideHCID 159612033-Methylamino-4-(2-mercaptoethylamino)-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-mercaptoethylamino)-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-95b3b9299d2c4993a9cb013df069040a
Source dataset
uspto-grants-1983_02
Patent number
US04374248

Reaction notes

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