Dihydrogenphosphate → 6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-N-[2-(morpholin-4-yl)ethyl]-1,3-benzothiazol-2-amine

HRID 517806Notes

Reaction equation

HRID 517806 reaction equation
P([O-])(O)(O)=O.SCC(C(CS)O)O.Cl[C:15]1[N:19]2[N:20]=[C:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH:22]=[CH:23][C:18]2=[N:17][N:16]=1.CC([C:35]1[C:40]2[N:41]=[C:42]([N:44]([CH2:48][CH2:49][N:50]3[CH2:55][CH2:54][O:53][CH2:52][CH2:51]3)C(=O)[O-])[S:43][C:39]=2[CH:38]=[C:37]([S:56]C#N)[CH:36]=1)(C)C>O.C(O)C>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C:21]2[CH:22]=[CH:23][C:18]3[N:19]([C:15]([S:56][C:37]4[CH:36]=[CH:35][C:40]5[N:41]=[C:42]([NH:44][CH2:48][CH2:49][N:50]6[CH2:55][CH2:54][O:53][CH2:52][CH2:51]6)[S:43][C:39]=5[CH:38]=4)=[N:16][N:17]=3)[N:20]=2)=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 1003DihydrogenphosphateHCID 190011,4-Dimercapto-2,3-butanediolHCID 446043783-Chloro-6-(4-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazineHCID 866478921,1-Dimethylethyl[2-(morpholin-4-yl)ethyl](6-thiocyanato-1,3-benzothiazol-2-yl)carbamate

Product 1

HCID 425986576-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-N-[2-(morpholin-4-yl)ethyl]-1,3-benzothiazol-2-amineYield 32.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

8 mg of dihydrogen phosphate in 1 cm3 of water, 680 mg of DL-dithiothreitol and 336 mg of 3-chloro-6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazine are added, at 20° C., to a solution of 636 mg of 1,1-dimethylethyl[2-(morpholin-4-yl)ethyl](6-thiocyanato-1,3-benzothiazol-2-yl)carbamate in 10 cm3 of ethanol degassed with argon for 5 min. The suspension is stirred at reflux for 18 h. The reaction is placed in a refrigerator overnight and then the greyish-white solid is spin-filter-dried. This solid is washed with diethyl ether and then made into a paste in dichloromethane and spin-filter-dried. 222 mg of 6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-N-[2-(morpholin-4-yl)ethyl]-1,3-benzothiazol-2-amine are thus obtained in the form of a greyish-white powder, the characteristics of which are as follows:

Workup

  1. customdegassed with argon for 5 min
  2. temperatureat reflux for 18 h
  3. customis placed in a refrigerator overnight
  4. customthe greyish-white solid is spin-filter-dried
  5. washThis solid is washed with diethyl ether
  6. customspin-filter-dried

Sources & evidence

ORD record
ord-247ea63b80294c9eb03d4b258065cd3d
Source dataset
uspto-grants-2015_08
Patent number
US09115134B2

Reaction notes

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