Dibutyltin oxide → HCID 178426571, compound

HRID 2223895Notes

Reaction equation

HRID 2223895 reaction equation
[C:1]([CH2:3][CH2:4][C:5]1([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([N:19]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][N:28]=3)[C:20]([C:22]3[O:23][CH:24]=[CH:25][CH:26]=3)=[O:21])[CH2:15][CH2:14]2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)#[N:2].C[Si]([N:38]=[N+:39]=[N-:40])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[NH:38]1[C:1]([CH2:3][CH2:4][C:5]2([CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][CH:16]([N:19]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][N:28]=4)[C:20]([C:22]4[O:23][CH:24]=[CH:25][CH:26]=4)=[O:21])[CH2:15][CH2:14]3)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)=[N:2][N:40]=[N:39]1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxide2×HCID 78378Azidotrimethylsilane2×HCID 10225756HCID 10225756, compound

Product 1

HCID 178426571HCID 178426571, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-[1-[2-[1-(2-cyanoethyl)cyclohexyl]ethyl]piperidin-4-yl]-N-(5-methylpyridin-2-yl) -2-furancarboxamide (355 mg) dissolved in toluene (2 mL) were added trimethylsilylazide (0.21 mL) and di-n-butyltin oxide (19.7 mg). The solution was heated under reflux for 11 hours. Trimethylsilylazide (0.42 mL) and di-n-butyltin oxide (98.0 mg) were further added to the solution and it was heated under reflux for 4 hours. The solvent was distilled off under reduced pressure (by azeotropic distillation with methanol). The resulting residue was purified by chromatography (silica gel, chloroform:methanol=80:20) to give the title compound (385 mg).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 11 hours
  3. temperaturewas heated
  4. temperatureunder reflux for 4 hours
  5. distillationThe solvent was distilled off under reduced pressure (by azeotropic distillation with methanol)
  6. customThe resulting residue was purified by chromatography (silica gel, chloroform:methanol=80:20)

Sources & evidence

ORD record
ord-f66b5a0d7ef84eb0a0c978f03c679b3a
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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