1,4-Dimercapto-2,3-butanediol → 1-[2-(4-Methylpiperazin-1-yl)ethyl]-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea

HRID 633488

Reaction equation

HRID 633488 reaction equation
[S:1]([C:4]1[CH:25]=[CH:24][C:7]2[N:8]=[C:9]([NH:11][C:12]([NH:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[O:13])[S:10][C:6]=2[CH:5]=1)C#N.SCC(C(CS)O)O>P([O-])(O)(O)=O.[K+]>[CH3:23][N:20]1[CH2:19][CH2:18][N:17]([CH2:16][CH2:15][NH:14][C:12]([NH:11][C:9]2[S:10][C:6]3[CH:5]=[C:4]([SH:1])[CH:25]=[CH:24][C:7]=3[N:8]=2)=[O:13])[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 190011,4-Dimercapto-2,3-butanediolHCID 866478811-(6-Thiocyanato-1,3-benzothiazol-2-yl)-3-[2-(4-methylpiperazin-1-yl)ethyl]urea

Product 1

HCID 866478801-[2-(4-Methylpiperazin-1-yl)ethyl]-3-(6-sulphanyl-1,3-benzothiazol-2-yl)ureaYield 40.7%

Reagents, catalysts & solvents 1

HCID 516951Monobasic potassium phosphateCatalyst

Procedure

The 1-[2-(4-methylpiperazin-1-yl)ethyl]-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea was prepared according to the method described in Example 1b, but using 1 g of 1-(6-thiocyanato-1,3-benzothiazol-2-yl)-3-[2-(4-methylpiperazin-1-yl)ethyl]urea, 14 mg of potassium dihydrogen phosphate and 1.16 g of DL-dithiothreitol. 380 mg of 1-[2-(4-methylpiperazin-1-yl)ethyl]-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea are thus obtained in the form of a white solid, the characteristics of which are as follows:

Workup

  1. customThe 1-[2-(4-methylpiperazin-1-yl)ethyl]-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea was prepared

Sources & evidence

ORD record
ord-9798316fa0f24c03bb298040c767c9d3
Source dataset
uspto-grants-2016_04
Patent number
US09321777B2

Linked notes

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