Toluene → HCID 86647890, compound

HRID 517804Notes

Reaction equation

HRID 517804 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16]([S:19][C:20]4[CH:36]=[CH:35][C:23]5[N:24]=[C:25]([NH:27]C(=O)OC(C)(C)C)[S:26][C:22]=5[CH:21]=4)=[N:17][N:18]=3)[N:15]=2)=[CH:6][CH:5]=1.[CH3:37][O:38][CH2:39][CH2:40]Cl.C1(C)C=CC=CC=1>CN(C)C=O.CO>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16]([S:19][C:20]4[CH:36]=[CH:35][C:23]5[N:24]=[C:25]([NH:27][CH2:40][CH2:39][O:38][CH3:37])[S:26][C:22]=5[CH:21]=4)=[N:17][N:18]=3)[N:15]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydrideHCID 86647874HCID 86647874, 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-91084f53654a47ed85c51ed4a9705908
Source dataset
uspto-grants-2015_08
Patent number
US09115134B2

Reaction notes

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