Chlorotrimethylsilane → HCID 59534566, compound

HRID 1507169Notes

Reaction equation

HRID 1507169 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-1c814b3b484b41daa7f8f5016dfcdb71
Source dataset
uspto-grants-2015_12
Patent number
US09221806B2

Reaction notes

Loading…