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

HRID 1702392Notes

Reaction equation

HRID 1702392 reaction equation
COC1C(OC)=NS(=O)N=1.[CH3:11][N:12](CC1SC=C(CSCCN)N=1)[CH3:13].[CH3:25][N:26]([CH2:28][C:29]1[S:30][CH:31]=[C:32]([CH2:34][S:35][CH2:36][CH2:37][NH:38][C:39]2[C:43](OC)=[N:42][S:41](=[O:46])[N:40]=2)[N:33]=1)[CH3:27].CNC>>[CH3:25][N:26]([CH2:28][C:29]1[S:30][CH:31]=[C:32]([CH2:34][S:35][CH2:36][CH2:37][NH:38][C:39]2[C:43]([N:12]([CH3:13])[CH3:11])=[N:42][S:41](=[O:46])[N:40]=2)[N:33]=1)[CH3:27]

Participants

5

Reactant 4

HCID 674DimethylamineHCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazoleHCID 129139473,4-Dimethoxy-1,2,5-thiadiazole 1-oxideHCID 204021103-{2-[(2-Dimethylaminomethyl-4-thiazolyl)methylthio]ethylamino}-4-methoxy-1,2,5-thiadiazole 1-oxide

Product 1

HCID 204021593-{2-[(2-Dimethylaminomethyl-4-thiazolyl)methylthio]ethylamino}-4-dimethylamino-1,2,5-thiadiazole 1-oxide

Procedure

When a solution of 3,4-dimethoxy-1,2,5-thiadiazole 1-oxide [prepared in Example 4, Step A] is reacted with one equivalent of 2-[(2-dimethylaminomethyl-4-thiazolyl)methylthio]ethylamine [prepared in Example 33, Step E] and the resultant 3-{2-[(2-dimethylaminomethyl-4-thiazolyl)methylthio]ethylamino}-4-methoxy-1,2,5-thiadiazole 1-oxide is treated with an excess of dimethylamine according to the procedure described in Example 28, the title compound is thereby produced.

Sources & evidence

ORD record
ord-30fcb0745847412591dd330d088baab3
Source dataset
uspto-grants-1983_04
Patent number
US04380639

Reaction notes

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