Triethylsilane → HCID 23503259, compound

HRID 1835146Notes

Reaction equation

HRID 1835146 reaction equation
C([SiH](CC)CC)C.O[CH:9]([C:16]1[S:30][C:19]2[C:20]([CH2:26][CH:27]([CH3:29])[CH3:28])=[N:21][N:22]([CH3:25])[C:23](=[O:24])[C:18]=2[CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O.ClCCl>[CH3:25][N:22]1[C:23](=[O:24])[C:18]2[CH:17]=[C:16]([CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[S:30][C:19]=2[C:20]([CH2:26][CH:27]([CH3:29])[CH3:28])=[N:21]1

Participants

6

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 23503258HCID 23503258, compound

Product 1

HCID 23503259HCID 23503259, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (1.0 ml) was added to a stirred solution of 2-[1-hydroxy-1-phenylmethyl]-5-methyl-7-(2-methylpropyl)thieno[2,3-d]pyridazin-4(5H)-one (example 14, 1.44 g) in trifluoroacetic acid (2 ml) and dichloromethane (10 ml) at room temperature. After 24 hours, saturated sodium hydrogen carbonate solution (100 ml) was added and the mixture was extracted with ethyl acetate (100 ml). The organic extracts were washed twice with saturated sodium hydrogen carbonate solution, then with brine, and then dried, filtered and evaporated. The residue was purified by column chromatography, eluting with ethyl acetate:isohexane (1:4 then 1:3), to give the title compound (1.11 g) as a solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (100 ml)
  2. washThe organic extracts were washed twice with saturated sodium hydrogen carbonate solution
  3. dry with materialwith brine, and then dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography
  7. washeluting with ethyl acetate:isohexane (1:4

Sources & evidence

ORD record
ord-cda96a77ab6b4ba19f0f7c4d503d9fcd
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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