Ethanol → 1-{6-[(6-Ethoxy[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(morpholin-4-yl)ethyl]urea

HRID 1035774Notes

Reaction equation

HRID 1035774 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]([NH:12][C:13]2[S:14][C:15]3[CH:21]=[C:20]([SH:22])[CH:19]=[CH:18][C:16]=3[N:17]=2)=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O)C.SCC(C(CS)O)O.Cl[C:35]1[N:39]2[N:40]=[C:41]([O:44][CH2:45][CH3:46])[CH:42]=[CH:43][C:38]2=[N:37][N:36]=1>O.P([O-])(O)(O)=O.[K+]>[CH2:45]([O:44][C:41]1[CH:42]=[CH:43][C:38]2[N:39]([C:35]([S:22][C:20]3[CH:19]=[CH:18][C:16]4[N:17]=[C:13]([NH:12][C:10]([NH:9][CH2:8][CH2:7][N:1]5[CH2:2][CH2:3][O:4][CH2:5][CH2:6]5)=[O:11])[S:14][C:15]=4[CH:21]=3)=[N:36][N:37]=2)[N:40]=1)[CH3:46]

Participants

7

Reactant 4

HCID 702EthanolHCID 190011,4-Dimercapto-2,3-butanediolHCID 67524522HCID 67524522, compoundHCID 866478761-(2-Morpholin-4-ylethyl)-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea

Product 1

HCID 425986581-{6-[(6-Ethoxy[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(morpholin-4-yl)ethyl]ureaYield 46.8%

Reagents, catalysts & solvents 2

HCID 516951Monobasic potassium phosphateCatalystHCID 962WaterSolvent

Procedure

The 1-{6-[(6-ethoxy[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(morpholin-4-yl)ethyl]urea was prepared according to the method described in Example 17a, but using 613 mg of 1-[2-(morpholin-4-yl)ethyl]-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea, 20 cm3 of degassed ethanol, 7 mg of potassium dihydrogen phosphate in 0.2 cm3 of water, 699 mg of DL-dithiothreitol and 300 mg of 3-chloro-6-ethoxy[1,2,4]triazolo[4,3-b]pyridazine. 354 mg of 1-{6-[(6-ethoxy[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(morpholin-4-yl)ethyl]urea are thus obtained in the form of a white powder, the characteristics of which are as follows:

Workup

  1. customThe 1-{6-[(6-ethoxy[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(morpholin-4-yl)ethyl]urea was prepared

Sources & evidence

ORD record
ord-f60aa43616f44124a61ea2f015acbe2a
Source dataset
uspto-grants-2013_10
Patent number
US08546393B2

Reaction notes

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