Toluene → HCID 86647890, compound

HRID 1035766Notes

Reaction equation

HRID 1035766 reaction equation
[H-].[Na+].[CH3:3][C:4]([N:7]([C:11]1[S:12][C:13]2[CH:19]=[C:18]([S:20][C:21]3[N:25]4[N:26]=[C:27]([C:30]5[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=5)[CH:28]=[CH:29][C:24]4=[N:23][N:22]=3)[CH:17]=[CH:16][C:14]=2[N:15]=1)C(=O)[O-])(C)C.[CH3:37][O:38]CCCl.C1(C)C=CC=CC=1>CN(C)C=O.CO>[F:36][C:33]1[CH:34]=[CH:35][C:30]([C:27]2[CH:28]=[CH:29][C:24]3[N:25]([C:21]([S:20][C:18]4[CH:17]=[CH:16][C:14]5[N:15]=[C:11]([NH:7][CH2:4][CH2:3][O:38][CH3:37])[S:12][C:13]=5[CH:19]=4)=[N:22][N:23]=3)[N:26]=2)=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydrideHCID 86647891HCID 86647891, compound

Product 1

HCID 86647890HCID 86647890, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

45 mg of sodium hydride at 60% in oil are added to a mixture of 263 mg of 1,1-dimethylethyl(6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)carbamate and 0.10 cm3 of 2-chloroethyl methyl ether in 3 cm3 of N,N-dimethylformamide at 20° C. The suspension is heated in a bath at 90° C. overnight. The cooled reaction mixture is coevaporated to dryness several times with toluene. The residue obtained is taken up in methanol. After paste formation for 15 min, the brownish-yellow suspension is spin-filter-dried. The insoluble material is washed several times with methanol. This solid is treated with 0.4 cm3 of trifluoroacetic acid in 3 cm3 of dichloromethane at 20° C. for 2 h. The resulting reaction mixture is concentrated to dryness under vacuum, to give 116 mg of 6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-N-(2-methoxyethyl)-1,3-benzothiazol-2-amine in the form of a yellowy-beige powder, the characteristics of which are as follows:

Workup

  1. customThe cooled reaction mixture
  2. customThe residue obtained
  3. customthe brownish-yellow suspension is spin-filter-dried
  4. washThe insoluble material is washed several times with methanol
  5. additionThis solid is treated with 0.4 cm3 of trifluoroacetic acid in 3 cm3 of dichloromethane at 20° C. for 2 h
  6. customThe resulting reaction mixture
  7. concentrationis concentrated to dryness under vacuum

Sources & evidence

ORD record
ord-aeb882b8c8c049e78fcc1ea253c16079
Source dataset
uspto-grants-2013_10
Patent number
US08546393B2

Reaction notes

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