Trifluoroacetic acid → HCID 9907010, compound

HRID 1835141Notes

Reaction equation

HRID 1835141 reaction equation
C([SiH](CC)CC)C.O[CH:9]([C:20]1[S:34][C:23]2[C:24]([CH2:30][CH:31]([CH3:33])[CH3:32])=[N:25][N:26]([CH3:29])[C:27](=[O:28])[C:22]=2[CH:21]=1)[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:29][N:26]1[C:27](=[O:28])[C:22]2[CH:21]=[C:20]([CH2:9][C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]=[CH:12][CH:11]=3)[S:34][C:23]=2[C:24]([CH2:30][CH:31]([CH3:33])[CH3:32])=[N:25]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 23503229HCID 23503229, compound

Product 1

HCID 9907010HCID 9907010, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylsilane (0.3 ml) was added to a solution of 2-[1-hydroxy-1-(1-naphthalenyl)methyl]-5-methyl-7-(2-methylpropyl)thieno[2,3-d]pyridazin-4(5H)-one (0.3 g) prepared as described in Example 6 above and trifluoroacetic acid (2 ml) in dichloromethane (10 ml). After 30 minutes, the reaction mixture was evaporated and the residue remaining was dissolved in ethyl acetate. The ethyl acetate solution was washed twice with saturated sodium hydrogen carbonate solution and once with brine, and then dried and evaporated. Purification by chromatography eluting with iso-hexane/ethyl acetate (4:1 to 2:1), and subsequent HPLC eluting with isohexane:ethyl acetate (2:1) gave the title compound (0.25 g).

Workup

  1. customprepared
  2. customthe reaction mixture was evaporated
  3. dissolutionthe residue remaining was dissolved in ethyl acetate
  4. washThe ethyl acetate solution was washed twice with saturated sodium hydrogen carbonate solution and once with brine
  5. customdried
  6. customevaporated
  7. customPurification by chromatography
  8. washeluting with iso-hexane/ethyl acetate (4:1 to 2:1), and subsequent HPLC
  9. washeluting with isohexane:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-8a43607a2afb4c68b3a88b12d26e1234
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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