3-Amino-1,2-propanediol → 2-[4-[2-[[4-(2,3-dihydroxypropylamino)-1,1-dioxo-1,2,5-thiadiazol-3-yl]amino]ethylsulfanylmethyl]-1,3-thiazol-2-yl]guanidine

HRID 1702359Notes

Reaction equation

HRID 1702359 reaction equation
N(C1SC=C(CSCCN)N=1)C(N)=N.COC1C(OC)=NS(=O)(=O)N=1.CO[C:28]1[C:32]([NH:33][CH2:34][CH2:35][S:36][CH2:37][C:38]2[N:39]=[C:40]([NH:43][C:44]([NH2:46])=[NH:45])[S:41][CH:42]=2)=[N:31][S:30](=[O:48])(=[O:47])[N:29]=1.[NH2:49][CH2:50][CH:51]([OH:54])[CH2:52][OH:53]>>[OH:54][CH:51]([CH2:52][OH:53])[CH2:50][NH:49][C:28]1[C:32]([NH:33][CH2:34][CH2:35][S:36][CH2:37][C:38]2[N:39]=[C:40]([NH:43][C:44]([NH2:46])=[NH:45])[S:41][CH:42]=2)=[N:31][S:30](=[O:47])(=[O:48])[N:29]=1

Participants

5

Reactant 4

HCID 735613-Amino-1,2-propanediolHCID 122305383,4-Dimethoxy-1,2,5-thiadiazole 1,1-dioxideHCID 178494332HCID 178494332, compoundHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 1785127152-[4-[2-[[4-(2,3-dihydroxypropylamino)-1,1-dioxo-1,2,5-thiadiazol-3-yl]amino]ethylsulfanylmethyl]-1,3-thiazol-2-yl]guanidine

Procedure

When a methanolic solution of 2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine is reacted with 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide by the procedure of Example 31 and the resultant 3-methoxy-4-{2-[(2-guanidinothiazol-4-yl)methylthio]ethylamino}-1,2,5-thiadiazole 1,1-dioxide is treated with 3-amino-1,2-propanediol, the title compound is thereby produced.

Sources & evidence

ORD record
ord-cf11c885aa504d1d9bf0cdc31b3f2d66
Source dataset
uspto-grants-1983_04
Patent number
US04380639

Reaction notes

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