Dibutyltin oxide → HCID 66682088, compound

HRID 530317Notes

Reaction equation

HRID 530317 reaction equation
[C:1]([N:3]1[CH2:8][CH2:7][CH:6]([N:9]([CH3:25])[C:10]([N:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[N:14]=[CH:13]2)=[O:11])[CH2:5][CH2:4]1)#[N:2].C([Sn](CCCC)=O)CCC.[N:36]([Si](C)(C)C)=[N+:37]=[N-:38]>C1(C)C=CC=CC=1>[N:2]1[NH:36][N:37]=[N:38][C:1]=1[N:3]1[CH2:8][CH2:7][CH:6]([N:9]([CH3:25])[C:10]([N:12]2[CH:16]=[C:15]([C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)[N:14]=[CH:13]2)=[O:11])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 86663118HCID 86663118, compound

Product 1

HCID 66682088HCID 66682088, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of N-(1-cyanopiperidin-4-yl)-4-(4-methoxyphenyl)-N-methyl-1H-imidazole-1-carboxamide (151 mg, 0.445 mmol) in toluene (10 mL) was added dibutylstannanone (13.84 mg, 0.056 mmol) followed by azidotrimethylsilane (0.207 mL, 1.557 mmol). The reaction mixture was heated at reflux for 5 h, whereupon it was filtered still hot and the resulting pink solid was washed sequentially with toluene, dichloromethane and then finally ether. The solid was recrystallised from methanol to give the product as a light pink solid, (100 mg, 56%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 h, whereupon it
  3. filtrationwas filtered still hot
  4. washthe resulting pink solid was washed sequentially with toluene, dichloromethane
  5. customThe solid was recrystallised from methanol

Sources & evidence

ORD record
ord-fdd5cb3da79844fcbaac81bd2b444524
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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