1,4-Dimercapto-2,3-butanediol → HCID 42598894, compound

HRID 633508Notes

Reaction equation

HRID 633508 reaction equation
[N:1]1([CH2:6][CH2:7][NH:8][C:9]([NH:11][C:12]2[S:13][C:14]3[CH:20]=[C:19]([SH:21])[CH:18]=[CH:17][C:15]=3[N:16]=2)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.P([O-])(O)(O)=O.[K+].SCC(C(CS)O)O.Cl[C:37]1[N:41]2[N:42]=[C:43]([O:46][CH3:47])[CH:44]=[CH:45][C:40]2=[N:39][N:38]=1>O.C(O)C>[CH3:47][O:46][C:43]1[CH:44]=[CH:45][C:40]2[N:41]([C:37]([S:21][C:19]3[CH:18]=[CH:17][C:15]4[N:16]=[C:12]([NH:11][C:9]([NH:8][CH2:7][CH2:6][N:1]5[CH2:2][CH2:3][CH2:4][CH2:5]5)=[O:10])[S:13][C:14]=4[CH:20]=3)=[N:38][N:39]=2)[N:42]=1

Participants

7

Reactant 4

HCID 190011,4-Dimercapto-2,3-butanediolHCID 516951Monobasic potassium phosphateHCID 21822186HCID 21822186, compoundHCID 86647895HCID 86647895, compound

Product 1

HCID 42598894HCID 42598894, compoundYield 23.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The 1-{6-[(6-methoxy[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(pyrrolidin-1-yl)ethyl]urea was prepared according to the method described in Example 17a, but using 547 mg of 1-[2-(pyrrolidin-1-yl)ethyl]-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea, 25 cm3 of degassed ethanol, 8 mg of potassium dihydrogen phosphate in 0.2 cm3 of water, 787 mg of DL-dithiothreitol and 313 mg of 3-chloro-6-methoxy[1,2,4]-triazolo[4,3-b]pyridazine. 189 mg of 1-{6-[(6-methoxy[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(pyrrolidin-1-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-methoxy[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(pyrrolidin-1-yl)ethyl]urea was prepared

Sources & evidence

ORD record
ord-7cb028c091f94273983d8d72c1a2fa82
Source dataset
uspto-grants-2016_04
Patent number
US09321777B2

Reaction notes

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