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 1980681Notes

Reaction equation

HRID 1980681 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[C:2]([NH2:4])=[NH:3].CO[C:17]1[C:21](OC)=[N:20][S:19](=[O:25])(=[O:24])[N:18]=1.[NH2:26][CH2:27][CH:28]([OH:31])[CH2:29][OH:30]>>[OH:31][CH:28]([CH2:29][OH:30])[CH2:27][NH:26][C:21]1[C:17]([NH:14][CH2:13][CH2:12][S:11][CH2:10][C:8]2[N:9]=[C:5]([NH:1][C:2]([NH2:4])=[NH:3])[S:6][CH:7]=2)=[N:18][S:19](=[O:24])(=[O:25])[N:20]=1

Participants

4

Reactant 3

HCID 735613-Amino-1,2-propanediolHCID 122305383,4-Dimethoxy-1,2,5-thiadiazole 1,1-dioxideHCID 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-thiadazole 1,1-dioxide is treated with 3-amino-1,2-propanediol, the title compound is thereby produced.

Sources & evidence

ORD record
ord-fe101fe53217410489db800ff07c8521
Source dataset
uspto-grants-1985_04
Patent number
US04510309

Reaction notes

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