Chlorotrimethylsilane → HCID 59534566, compound

HRID 2088366Notes

Reaction equation

HRID 2088366 reaction equation
C[Si](C)(C)[Cl:3].N[C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:13]=[C:14]([CH:31]=[CH:32][CH:33]=2)[CH2:15][N:16]2[C:21](=[O:22])[CH:20]=[CH:19][C:18]([C:23]3[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=3)=[N:17]2)[N:8]=1>ClCCl.N([O-])=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:3][C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:13]=[C:14]([CH:31]=[CH:32][CH:33]=2)[CH2:15][N:16]2[C:21](=[O:22])[CH:20]=[CH:19][C:18]([C:23]3[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=3)=[N:17]2)[N:8]=1

Participants

5

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 59534591HCID 59534591, compound

Product 1

HCID 59534566HCID 59534566, compound

Reagents, catalysts & solvents 2

HCID 3015282Tetrabutylammonium nitriteCatalystHCID 6344DichloromethaneSolvent2×

Procedure

37.2 1.14 ml (9.00 mmol) of trimethylchlorosilane are added to a suspension of 381 mg (1.00 mmol) of 2-[3-(5-amino-1,2,4-oxadiazol-3-yl)-benzyl]-6-(3,5-difluorophenyl)-2H-pyridazin-3-one in 5 ml of dichloromethane. A solution of 865 mg (3.00 mmol) of tetrabutylammonium nitrite in 3 ml of dichloromethane is slowly added dropwise to this suspension at room temperature with stirring. After the reaction mixture has been stirred at room temperature for 16 hours, it is filtered. The filtrate is partitioned between dilute sodium hydrogencarbonate solution and dichloromethane. The organic phase is dried over sodium sulfate and evaporated, giving crude 2-[3-(5-chloro-1,2,4-oxadiazol-3-yl)benzyl]-6-(3,5-difluorophenyl)-2H-pyridazin-3-one as yellowish oil, which is employed for the next reaction without further purification; ESI 401.

Workup

  1. stirringAfter the reaction mixture has been stirred at room temperature for 16 hours
  2. filtrationit is filtered
  3. customThe filtrate is partitioned between dilute sodium hydrogencarbonate solution and dichloromethane
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-f40f29cf912c4bc9b28dbebe5d6ec10c
Source dataset
uspto-grants-2013_05
Patent number
US08435981B2

Reaction notes

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